


He Didn't Have To Be

by turningthepages



Series: He Didn't Have To Be [1]
Category: Supernatural
Genre: (I've realized how sad these tags sound), (John), (Mary) - Freeform, (i think), (mostly fluff though), (there might be a bit of angst), (this is honestly very fluffy), Alternate Universe, Angst with a Happy Ending, Castiel is a Sweetheart, Dean Has Self-Worth Issues, Dean is 23, Dean is raising Sam, Death in Childbirth, Epilogue, First Dates, First Kiss, Fluff, Implied/Referenced Suicide, Light Angst, M/M, Mechanic Dean, Past Character Death(s), Sam is 3, Teacher Castiel, Tooth-Rotting Fluff
Language: English
Status: Completed
Published: 2017-02-13
Updated: 2017-04-08
Packaged: 2018-09-23 23:11:30
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 36,410
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9686360
Author URL: https://archiveofourown.org/users/turningthepages/pseuds/turningthepages
Summary: Twenty-three, working on classic cars every day, making decent money, getting home cooked meals every Sunday, Dean is content. He's also ready to meet someone and settle down. He's young and stable so it should be simple, right? The problem is Dean has yet to find someone who doesn't run for the hills when he tells them that he has a three-year-old at home.Life threw some pretty crappy cards Dean's way, and he's doing the best he can with what he's got... is it possible that someone out there may actually be interested in the beautiful mess Dean calls his life?





	1. Chapter 1

“Sammy, it’s a million degrees outside. You cannot wear your snowsuit buddy.” This was Dean’s fourth attempt at getting a t-shirt on the kid and it was proving more and more impossible. He was cursing Sam’s newfound ability to open doors, or else he would never have opened up the hall closet, found his snowsuit, and vehemently insisted that he go play in the snow in the dead heat of summer. 

Now on Dean’s fifth try to force thrashing arms into the sleeves, he was about to lose his cool. Kneeling to eyelevel Dean attempted to level his voice, stern but still warm, he hoped. 

“Stop crying. It’s too hot. Sammy, come on, let me put on your t-shirt. We have to go over to Grandma and Grandpa’s. They’re waiting to see you. Don’t you want to see them?” 

A swift slap to the face was the answer he got in return. “No! Do not hit Samuel. You need to stop that now or we aren’t going swimming today.” 

Though Dean’s threat was empty at best, (the guy needed a damn break) Sam didn’t angrily hit him again and Dean counted that as a win. Still, he now struggled to wrangle their bag, with their change of clothes for later, over his shoulder while attempting to get Sam to let him pick him up. 

“Okay. Okay. It’s just going to be one of those days.” Dean grumbled to himself in defeat as he successfully hauled a kicking and screaming, half-dressed and pissed off toddler out the door. 

“Please, Sammy, you’ve got to stop crying.” He could see the neighbors from across the street giving him their less than welcome icy glares. Now having to deal with it on an at least weekly basis, Dean regrets ever looking at single parents (or any parents really) with disgust when they couldn’t get their screaming infant under control. 

Back then it seemed easy. Back then he had though ‘If you don’t spoil your damn kids then they wont ever act like a little terror.’ He hadn’t actually considered that calming a toddler in the midst of a tantrum was often equivalent to defusing a bomb wearing a blindfold with your arms bound behind your back. 

It was nearly twice as hard to get the three-year-old into his car seat, not pausing his thrashing long enough to get his arms through the straps. If Dean weren’t so high strung at the moment, he might actually laugh at the state of his most prize possession, his '67 Chevy Impala, gifted to him on his high school graduation day; the car he swore he would forever care for like the true lady that she is. Now littered with toys, random socks and mismatched shoes, crumbs from all of Dean’s attempts to keep Sammy distracted with food, and mud stains on practically every surface that Sam’s feet hand managed to reach, the car looked more like a toddler shuttle than the beauty Dean knew her to be. One day, Dean told himself, he’d have the time to restore her to her former glory. Like when Sam graduated college. If he were lucky. 

“Samuel Henry Winchester cut it out or so help me I will take your books away!” Dean gritted through clenched teeth, now trying to get the kid to let him buckle the safety straps. The threat caught Sam’s attention, and Dean knew by beat-red hue to the baby’s face that he was in for an ear-splitting wail. 

He knew better than to threaten to take Sam’s books away, really he did. It always resulted in the same meltdown, but apparently he never learned from his mistakes, and could not be trusted to make wise decisions while frustrated. 

“Damnit” He whispered under his breath. 

The now shrieking toddler kicked and threw anything in reach in the backseat of the Impala. Dean knew it was impossible for all of the surrounding houses to not hear Sam's cries. It seriously, took every sheer ounce of willpower in that moment for Dean not to slam the car door shut, but lord did he want to. He knew better though. He knew what it would look like to those watchful eyes from across the street. It would have just given them more reasons to see him unfit to be raising Sammy, not like they didn’t already have a complete dissertation on that subject matter, but he wasn’t about to add more fuel to the fire. 

Dean loved days like these. 

By the time they got to Bobby and Ellen’s Sam had calmed down marginally. It was enough that Dean was able to get him out of the car without much of a fuss. Sam still was adamant that he did not want to be held, and Dean decided that was a battle he didn’t need to win. 

Letting Sam teeter his way to the front door while Dean carried their bag, he took notice of the cars he saw in the parking lot. It looked like most of the regular family members were already at the small get together. Dean noticed Jody’s car straight away as it was parked next to some gold monstrosity pimpmobile he’d never seen before (he had to find out who owned that beast, in order to make fun of them with Bobby later), but he didn’t see the car he was hoping to: Jo’s sky blue Chevelle. The one Bobby had gotten for her on her 16th birthday. She hadn’t been home from college since President’s Day and Dean was severely missing his best friend. The get together was to celebrate her successfully completing her first year in college. And damn was Dean proud of her for it.

Not bothering to knock, Dean let himself and Sammy into the house veering left to go drop their things off in the guest bedroom. 

“Bobby? You in here?” Dean called out from the bedroom. 

“Kitchen!” He heard the gruff voice answer in response. 

“Grandpa!” 

The squeal was followed by the pitter patter of tiny feet on the hardwood floor as Sam excitedly ran in the direction of the kitchen. If Dean weren't so high strung over the seemingly endless screams that he'd just been graced with, he might have thought that little run was cute. (Okay, it was freaking adorable). He just thanked the sky above that Bobby'd at least be able to get the kid out of his bad mood. Sam worshiped the older man. 

After grabbing out some pool towels and sunblock from the bag, Dean walked down the hallway towards the kitchen. He saw Bobby grabbing one of Sam’s favorite strawberry popsicles from the freezer (popsicles he always made sure to keep stock of) talking away to Sam about some dog character on Sam's favorite TV show like it was Bobby's favorite topic of conversation. The old man was seriously wrapped around the kid's finger and he didn't care who knew it. Already Sam was in an infinitely better mood than he had been with Dean. Dean knew as long as he kept his distance and let Bobby keep Sammy entertained, there wouldn't be anymore outbursts at least until the sugar rush ended.

“He is in rare form today. Don’t let his cute face fool you.” Dean warned by way of greeting, making Bobby laugh.

“That’s because he has to deal with you every day. I’d act out too.” 

“Screw you.” 

Dean knew Bobby was just making jokes, but he was a little peeved in general. Trying to shake his crap mood away, he knelt down to slather some sun lotion on the toddler while Sam was distracted by the popsicle dripping down his arm and onto the floor.

“Oh that's how it's gonna be? I was just about to offer to watch him for you for the day so you could relax.” 

Dean pulled himself up off the ground and went to go grab a popsicle for himself. He knew Bobby was still just bustin' his balls and didn't even slightly take offence to Dean's little outburst (let's be real Dean had had far worse in the past), but he still knew that Bobby didn't deserve to be snapped at like that. “Sorry Bobby. I'm just... I'm sorry." He huffed out a frustrated sigh and shook the tension out of his shoulders before putting on a collected face. "We both know you’re going to watch him for me anyway though, you're fooling no one with your hard ass-ness. Kid loves you more than he’ll ever love me.” 

“That’s just because you’re the one who gives him consequences. I get to be fun Grandpa Bobby and spoil him with food.” 

“Want to switch roles then?” 

Dean casually leaned against the counter and stared at Sam making a mess on the floor too preoccupied with smearing the liquid sugar onto the tile than paying attention to the adults at the moment. He could see the concern in Bobby's eyes and felt himself crumbling under the stare. “I’m just--fuck. I'm starting to think the kids hates me, like legitimately hates me. And I am halfway positive the neighbors think I am torturing him because all he does is scream at me all the time. I wouldn’t put it past them if CPS were called on me. I'm literally just biding my time until they show up and take him from me.” 

“He’s three years old. He’s going to have bad days. Don’t mean you’re not doing your job correctly. And for the record, when he’s not screaming his lungs out the boy looks at you like you’re his whole world, because you are and you're doing right by him no matter what you think. Don’t ever forget that, son.” 

Despite it being what he wanted to hear, Dean knew he’d forever have difficulties hearing praise in the way he was raising Sammy. Deep down Dean knew he wasn’t doing that stellar of a job, he was hardly twenty three, working down at Bobby’s shop just to pay the bills, and relied on Ellen and Bobby’s Sunday dinner leftovers to get him and Sam through most of the week because he downright refused to take a pay raise without earning it the hard way. It wasn't an uncommon thought of his if he were even spending enough time with the kid, as it seemed Sam was mostly in the care of family members of his sitter during the day while Dean had to work. It's no wonder Sam had been acting out more recently, trying to get any form of attention from Dean since Dean wasn't doing this parenting thing right. 

He shrugged off Bobby's words and used the need to clean up Sam’s mess as an excuse to not take the praise. “Yeah, yeah. Enough of the feelings talk. Are you sure you’re good to keep an eye on him?” 

“This ain’t my first rodeo.” 

“Just give him to me if he get’s too much.” He knew Bobby could handle Sam, it wasn’t like the kid was particularly difficult, Dean just felt bad with how often he seemed to leave Sam in the care of others. 

“I know how to handle a fussy toddler. I think I’ll manage. You owe me one though.” 

“Yeah, yeah. Thanks old man.” He joked listlessly. He handed the pool towels and the extra sunblock to Bobby. 

“Get out of here before I change my mind.”

"Grandpa, can I go on the boats?" 

"As long as you put your floaties on without whining."

"De got me new floaties. They paw patrol.

"What? No way. I'm jealous. Come on, let's go put on your paw patrol floaties then and show them off." 

Dean shook his head with a smile on his face as he watched Sam book it out the back door into the direction of the gated pool. As Bobby turned and gave Dean a fond eye roll at Sam's antics, Dean silently thanked the man for being so good to him and Sam. He honestly didn't know how he could have done any of this without him. He refused to think what he'd do if he didn’t have Bobby _and_ Ellen in his life. 

He’d known them both since birth, was about five when the two of them tied the knot, spend most of his childhood working beside Bobby and John in the garage, learned all of his bartending skills from Ellen herself. It was them two who didn’t hesitate for a second to pay the majority of Dean’s bills when all shit hit the fan. It was them two who helped secure a job for Dean that let him still have enough time to be an active part of Sam’s life. It was them two who were always one phone call away if either he or Sam needed anything. It was them two who had always been a second set of parents to Dean, and now readily stepped in to be the parent figures Dean still often needs at his barely-an-adult age. 

His thoughts were getting a little more muddled than he wanted for the day, so he did his very best to shake the funky mood he was in away. He knew if he let on to Ellen that he was having a rough day he'd be smothered with feelings talk and he just wasn't up for that now. Not until Jo was there at least. So, as he made his way through the sliding door and out back, finding Ellen talking with a few of her neighbors on the deck by the pool, he plastered as sincere of a smile on his face. 

“Hey,” Dean greeted with a kiss to her cheek. 

A bright smile washed over Ellen’s face almost immediately. “Hey handsome, where’s the baby?” 

“Bobby took him. Swear the kid was possessed by the devil this morning.” 

Ellen and her friends all laughed in unison. “Why? What happened?” 

Dean pulled up a chair and slid in, grabbing a handful of grapes from the fruit platter that was sitting on the table in front of him. Since all the ladies at the table had been his mom's friends as well, Dean didn't really feel the need to greet them with anything more than a smile. They were basically his aunts, Missouri, Jody, and Donna. Ungracefully Dean shoved the fruit in his mouth and recounted the events from the morning. 

“Long story short I wouldn’t let him wear his snow suit and then accidently threatened to take his books.” 

“You’re downright awful aren’t you? Kid is completely justified." The amusement in Ellen's voice was apparent, and it made Dean crack a real smile. That is until she whacked him on the side of the head. "And for the love of God, you weren’t raised in a barn, could you wait to finish chewing before speaking?” 

“Sorry…” Dean took the time to actually swallow his food this time. Glaring and Donna who thought the altercation was hilarious. “But yeah, anyway, Sam thought he was justified too. Threw in a good bitch slap as his way to stick it to me.” 

“He hit you?” Ellen asked with wide, shocked eyes. 

“Yeah. S’been doing that a lot lately when I tell him no. I try and put him in time out for it but I don’t think it’s working.” 

The first time Sam had hit him Dean had been too shocked to even react more than just putting the kid in time out. But as this hits happened more, Dean didn't think his stern talks and time-outs were going to cut it anymore. Ellen seemed to understand that Dean needed some guidance. 

“I don’t know if this will work, but Sammy’s a pretty smart kid and I think that if you try and calmly talk to him about it he might stop. Tell him that when he hits you that it really hurts you. I think it'd really make him stop and think about it because the last thing he wants to do is hurt his De.” 

Dean nodded not knowing if Ellen was right about Sammy not wanting to hurt him, but he'd give it a try. It could work. “I’ll try it. I just don’t know how calm I can stay when the kid slaps me in the face.” 

“I’ve yet to see you actually raise your voice with that kid. I think you’ll be just fine.” She smiled proudly at Dean who shied away from the praise lest she see his parenting doubts blazing in his eyes. Evidently it worked, or Ellen just didn't want to call him out in front of the other ladies. (More than likely the latter). “Now, I know you don’t want to socialize with some old ladies, go on and have some fun.” 

“Jo isn’t even here yet.” Dean protested, looking around futilely for any signs of his best friend. 

“I don’t care. You spend all your time either with a fifty-year-old man, or a three-year-old one. You need some friends your own age. So go and talk to the ones here.” 

“Yes ma’am.” 

“And don’t worry about Sammy today. When he wears Bobby out, I’ll take him.” 

Dean stood and added another kiss to her cheek. “You're both a godsend.” 

“We know.” 

Dean took the time to make his rounds and say hi to the people that he knew. The backyard was scattered with a few of Jo’s friends from high school that Dean never really associated with but still greeted kindly. Most of them were goofing off in the pool, and Dean really just wanted to kick back with a beer and relax instead of try and associate with people he had little in common with. He decided to make a beeline for the beer the second he could. 

It was ten degrees hotter than the weather forecast had predicted and Dean was seriously regretting his outfit choice for the day. Like Sammy, he must have been craving colder weather when he was getting ready because a band t-shirt paired with a plaid button up (albeit short sleeved) was not exactly summer appropriate. Everything was sticking too him, making him extremely uncomfortable and he wondered to himself if it would be weird to go shirtless at this thing. There were just a few too many non-family members around for him to not feel self-conscious though.

Dean at least had his past self to thank for having the forethought to have Sammy wear his swim shorts to the barbecue or else he’d probably be dealing with a toddler running around in the buff refusing to put his pants back on. Though that sight might have been hilarious, with all these random people around, he wanted to avoid them judging him for something like that.

He took a moment to scan the backyard for sight of Sammy, even though he knew he had nothing to worry about if Bobby was with him. Satisfied with seeing Bobby guiding Sammy around the pool, Dean walked over to the coolers to grab himself a much needed drink. The drinks were further away from the group, almost on the side of the house where most of the shade was collecting, and Dean seriously wondered if anyone would notice him hiding out over there. He wagered that Ellen would find him in under ten minutes. The thought was amusing enough that he had a smile on his face when he rounded the corner. Standing at the large white ice chest, the one that always housed all the beer, Dean noticed a man he’d never met before but vaguely recognized from his quick greetings from earlier. The guy looked mildly uncomfortable, staring at the different selections of beer Ellen and Bobby always had a surplus of from the bar, which they unloaded at family barbecues. 

Dean usually wasn't one to stare but there was something immediately alluring about the other guy. Maybe it was the fact that Dean hadn't known him since high school, or maybe it was the fact that he had on tight fitting jeans and white button up shirt at a _pool party._ Regardless that the guy might've been a bit overdressed, Dean couldn't help but think how _nice_ the guy looked. And he'd yet to see the front of him...

The man hadn’t looked up from the cooler yet, and not wanting to be caught staring like a creep, Dean shook the fog out of his brain and attempted to sound casual in his greeting. 

“Uh. Uh, if you’re having a hard time deciding just close your eyes and reach in. It’s all pretty damn good if I say so myself. Ellen’s too good for some of that piss water people drink.” 

The slight twitch of the guys' shoulders lent Dean to believe he'd startled the stranger.The guy looked around himself for a moment too, as if wondering if he were the one being addressed before making eye contact with Dean.

Now, Dean can't say that he's a person who's typically drawn to people's eyes. If he were held at gunpoint he probably couldn't even tell you what his exes eye colors had been. No, it'd always been a smile that'd usually did him in but the man before him made Dean question why he didn't pay eyes more attention. Well, maybe because no one he'd ever met has had eyes like these. Incredibly kind and utterly blue, eyes that made Dean wish he'd seen them before. He felt awestruck for a moment, until he realized the the guy had more face to look at. And man, was he far more attractive than Dean had anticipated. Black bed-head that looked purposeful, the perfect amount of scuff with pouty pink lips, and a height and build similar to Dean’s own. He was better than any fantasy man Dean could have created himself. 

“Thank you. I guess I’ll give your method a try.” The stranger smiled to Dean before blindly reaching in and pulling out some obscure brand of beer Dean had yet to try. Probably some tester brand trying to get Ellen to sell at the Roadhouse. He watched as the guy opened the bottled and sampled it thoughtfully before nodding his head in satisfaction. His blue eyes shone happily. “It was wise to trust you.” 

Dean couldn’t fight back his smile and decided instantly that he wanted to get to know this guy. Trying to be nonchalant, he walked and grabbed the same drink the other man had before outstretching his hand. “I haven’t seen you at one of these things before. I’m Dean.” 

“I’m Castiel.” The guy, Castiel, replied taking Dean’s hand in a firm shake. “I’m Jody’s nephew. I actually recently moved in with her while I attempt and find someplace to live out here.” 

Dean didn’t want to get ahead of himself, but his thoughts quickly went to how he hoped that meant he’d see more of this guy in the future. “Oh? Where’d you move from?” 

“Illinois.” 

“Chicago?” Dean asked impressed. He always wanted to go see a big city.

Castiel laughed and shook like this was a common question people asked him. “No. Pontiac.” 

Struggling to sift through his high school geography information and place that city, Dean admitted, “Never heard of it.” 

“Not many people have. It’s definitely not Chicago.” 

“So why’d you move to Lawrence?” Dean asked taking a sip of the beer, which as always was pretty good.

“I wanted a change of scenery and Jody suggested I try it here. Who knows maybe next year will find me somewhere else.” 

“I can understand that.” Dean was definitely rusty at best with small talk these days, so he floundered for a minute on what people would generally ask next. Eventually he came up with, “What do you do?” 

“I’m a teacher. I finished the school year at my previous school two weeks ago but I have another job at the middle school lined up for the end of summer." Dean looked over the guy, Castiel, and assessed. With a pair of glasses and a tie, he could see the man being a sexy teacher. He knows he would've tried to be teacher's pet... He blushed a little at the thought, he was getting way in over his head. "How about you," the man asked, unaware of Dean's thoughts, "what do you do?” 

“Oh, I work with Bobby at his shop.” Dean shrugged. He knew it wasn’t an impressive occupation, but he was good at it and it paid the bills. 

Castiel nonetheless seemed impressed with Dean’s response and smiled at him kindly. “You might be seeing me soon then as Bobby told me I had to bring my, and I quote, hunk of shit death trap on wheels, in to get checked out.” 

Dean’s eyes widened comically knowing exactly the type of car Bobby would call that. “Don’t tell me you own the pimpmobile parked in front of the house. I feel like I shouldn’t even associate with you anymore out of sheer embarrassment in your choice of car.” 

Castiel laughed, a sound that instantly brightened Dean’s day. “Hey, nobody said teachers were made of money. It’s what I could afford.” 

That was it. The moment Dean realized he had to get to know everything he could about this man. It probably (more than likely) wouldn't go anywhere but he mustered up the courage to ask, “You want to sit down?”

“I’d like that.” Castiel said with a nod. 

The two of them made their way to a card table placed out in the grass with some foldable chairs. It was away from the enclosed pool area where the bulk of people were congregated and it was out of earshot from all the ladies at their patio table. Dean quickly scanned for Sam, checking in the way he seemed programed to, and saw him still happily splashing away so Dean turned his full attention back to Castiel as they sat down.

“So a teacher huh? What grade?” 

“I use to teach third grade, but when I was interviewing at schools around here the only position available at the time was in 6th. I’m not expecting it to be a good fit for me but I needed the job. I’m hoping something in the primary grades will open up for the following year.” 

Dean wondered how anyone in their right mind would willingly choose to spend their days with thirty or so prepubescent teenagers. Still, he commended those who did because he knew they must have the patience of saints. “If the kids are anything like I was in middle school, you’re probably in for it.” 

“That’s not encouraging.” Castiel said with a blank expression, though his quivering lip told Dean he was fighting back a smile. 

“Sorry man.” Dean knew he had a goofy smile on his face, but this was the first attractive person he’d spoken to in well over a year. He just hoped the other man was interested in him the way that he was interested. “So you said you’re Jody’s nephew?” 

“Yes. She and my mother are sisters.” 

“Oh cool. Is she the only one you know here?” Dean didn’t exactly know how to ask if Castiel came here alone without being too forward. 

“I met Ellen and Bobby when they had us over for dinner last Friday night. And I also know their daughter Jo. Long story short she wanted to visit Chicago, Ellen told Jody, Jody suggested Jo stay with me, despite Pontiac being a while away from Chicago, and I wound up being a makeshift tour guide for spring break.” 

“Oh so you’re the mysterious friend Jo spent spring break with. I thought she’d actually been spending time with a boyfriend or something and didn’t want to tell me.” 

“You and her are close?” Castiel asked.

Dean nodded. “We’re practically siblings. Known her all my life, we seriously grew up together.” 

Realization dawned on Castiel’s features. “You’re the best friend she wouldn’t shut up about.” 

“That would be me.” Dean said smugly. 

“She told me about some of your many adventures.” Castiel’s face looked like he knew some juicy stories and Dean’s eyes widened, slightly frightened. 

He hoped that since Jo hadn’t really known Castiel all that well she wouldn’t have spilled all of Dean’s deep dark secrets. “I wish I could say she’s a big fat liar, but sadly she’s not.” 

Castiel sat up straighter and leaned in towards Dean, intrigued. “You two really stole one of Bobby’s cars and drove it to Stull cemetery to see if you could find ghosts?” 

He couldn’t suppress his laugh. It wasn’t the worst thing the two of them had done, but it was still up there. 

Dean spent the next thirty minutes recounting that particularly rebellious night of his life. He’d had his learner's permit for a few solid months at that point, and he and Jo had spent the entire night researching the most haunted places in America. That had been their thing ever since he could remember; researching scary places, watching horror movies, trying to convince their families to let them investigate haunted houses. When they read about the cemetery they knew they needed to check it out for themselves. Jo managed to convince Dean to drive one of Bobby’s cars off of the property and the two of them set off at one in the morning with their flashlights and EMF detectors (purchased off eBay) to find the supernatural. 

They’d hardly been able to get out of the car when Ellen bounded out of her own and laid it into them thick. She’d apparently heard Dean’s fumbling to get the old car started and tried to run out after them. Dean had never in his life seen Ellen so angry, and later, after he’d driven the car back to his home with Ellen tailing behind him, Dean had to not only face Ellen’s still fuming anger but both his parent’s as well. It took Bobby weeks to even look Dean in the eye again, and that was even after Dean and Jo spent every day of the rest of their summer scrubbing Bobby’s shop from top to bottom as well as washing any and every car, inside and out, that came into the shop during that time. 

“What my parents and Ellen don’t know is that when my parents finally let me get my license I took Jo back out there. We were so excited to finally have the chance to be out there, but no joke, the two of us barely lasted thirty minutes before we thought we were going to shit ourselves and went back home.” 

Again, Castiel’s laugh made Dean feel on top of the world. He wanted to hear it more. “Here I was thinking that sneaking into three movies in one night was rebellious.” 

“Quite the bad ass, aren’t you there Castiel?” Dean joked flirtatiously, throwing in a wink, too, for good measure. 

“More so than you, I believe, Dean.” Castiel’s smile was enrapturing but the faint blush that captured his cheeks and caused him to look at his lap was what did Dean in. He had to actually pry his eyes away from the other man in order to speak again. Dean already had it bad for the guy. 

“So how did you get a name like Castiel? If you don’t mind me asking, it’s just not a very common name.” 

“My father claims the night he found out my mom was pregnant he had a dream that an Angel of the Lord named Castiel spoke to him, wanting to use him as his vessel to save the world. Or in other words, my dad was high as a kite, thought the name was cool, and my equally as stoned mother agreed with him.” 

Dean threw back his head in a thunderous laugh, because he hadn’t expected _that._ It was even better than Dean being named after his grandmother. “Tell me you’re the only one who had to suffer your parent’s quality naming system.” 

“I think Claire got off much easier than I did. They’d sobered up long before creating her.” Castiel tipped his beer in Dean’s direction before bringing it to his lips. Transfixed, Dean couldn’t help but stare as the man took a long swig of his drink. 

It’d been a while for Dean. Sue him.

“So you’ve got a sister?” Dean asked once he pulled his mind out of the gutter. Castiel nodded in response. “That’s cool. I always wanted one; one related by blood, because Jo would kill me if she ever heard me says he wasn’t my sister. 

“Sisters are alright but mostly a pain though. You might have gotten off easy with not actually having to live with your ‘sister.' Do you have any bothers? Since you weren't _blessed_ with a demon... I mean a 'sister'?” 

The question was one Dean knew he almost backed himself into, but still didn’t know how to answer. Before he could think of anything to say though, Sammy waddled over on his overly tired chucky legs and silently gestured up for Dean to hold him. Dean saw Bobby heading over to collect Sam, but Dean waved him off. The older man looked exhausted, and it was probably a good time to put Sam down for a nap anyway. 

“Hey bub, you tired?” Dean asked down to the kid, still holding his arms up for Dean to grab him. Sammy only managed a weak nod of the head and without another thought Dean picked up the exhausted toddler and adjusted him into a comfortable napping position over his shoulder. It’d taken him less than a second to forget about the company he had been keeping until he heard the other man’s surprised voice. 

“Oh,” Castiel said with the same level of shock Dean had grown use to hearing from others. “Oh, uhm. Is he yours?” 

Dean cringed, he’d been so caught up in recounting childhood memories that the two of them had hardly gotten to the basic ‘get to know you’ questions. Hell, Dean didn’t even know if the guy was into guys, and if he were, it left Dean wondering how long it was until this guy tried to escape the conversation. Dean knew finding out about Sammy was generally the catalyst for the conversation to be over. He’d long since grown use to the half-formed excuses men came up with the moment they learned about Sammy, leaving Dean coughing in the dust they kicked up in their haste to make a break for it. Dean didn’t even bother telling people Sam was 'technically' his brother because no matter the situation, a kid was a kid and some people just didn’t want to deal with that sort of baggage. 

Not knowing what to do, Dean nodded his head. He wanted to hold out hope that this guy would still try and talk to him even though he’d just found out Dean had a three-year-old. The puzzled look on Castiel’s face told Dean that he was still trying to process the situation. 

“Yeah, he is.” 

Castiel seemed to be trying to shake the cobwebs from his head before he spoke again. “He’s… he’s adorable. How old is he?” Though it was an innocent question, it seemed forced. 

“Just turned three last month.” 

“What’s his name?” 

Dean tried to not be surprised by the guy’s seeming interest in Sam, most guys had the curtesy to pretend for about three whole minutes that they cared about kids before they politely 'had to take off for an emergency.' Even not knowing the guy long, Dean could still read it in the other man’s eyes that he was disappointed. Though it wasn’t as potent as the looks most guys gave him at this point, Dean swore he could see a hint of the ‘you should have mentioned sooner that you had a kid so I wouldn’t have wasted time on you’ look. 

“Samuel goes by Sammy though.” His tone was deflated. He knew this conversation was going nowhere fast.

“And may I ask about his mother?” Castiel asked awkwardly. 

Dean tried not to flinch at the question. “Not around anymore.” 

“So it’s just you and him?” 

“Yup.” Dean felt Sammy snuggle closer into him, now completely dead to the world, and it made striking out with Castiel not seem so bad. Knowing that even when he was having a bad day Sammy still sought Dean out for comfort made him feel like he was doing something right. Before Dean and Castiel fell into any sort of awkward small talk about Sammy, Dean heard Bobby’s ‘dad’ voice from the patio. Giving him a temporary reprieve for his disappointment in striking out.

“It’s about damn time you showed up. We’re all here to celebrate your arrival yet you keep us all waiting.” 

“Well I’m sorry daddy, but I just have too many friends who didn’t want to see me go. I got caught up.” Jo sassed back goodheartedly. 

If he didn’t have a sleeping baby over his shoulder he would have probably pounced on her. Instead he waited patiently for her to say her hellos to the other guests. She didn’t make him wait too long. 

“Well if it isn’t Miss Joanna Beth.” Dean said with a wide smile when she finally made her way over to his side of the yard. Bobby, Ellen, and a few of Jo’s friends from high school followed behind, finding seats and bringing some foldable tables over. 

“Is that the ugliest son of a bitch in town I hear?” Jo asked leaning over the back of Dean’s chair to wrap both him and Sam in a hug. 

“You’re just still bitter that I bat for the other team. Everyone knows you had it bad for me when we were kids.” 

“You keep telling yourself that.” She shot back, though everyone at the table knew Dean’s jest held some truth to it. Jo quickly pulled up a chair and scooted close enough to Dean’s that she could sling her arm through his and rest her head on his unoccupied shoulder.

“I missed you.” Dean said honestly giving her a chaste kiss to the forehead.

“I missed you too. College is a lot different than I expected.” Jo supplied quietly enough so that others wouldn’t hear. There seemed to be something in her voice that hinted at her wanting to talk about it, but Dean knew better than to ask in front of family. 

“Still liking it though?” 

“I love it.” Jo looked up smiled at him. That’s when she seemed to notice Castiel sitting over to Dean’s right. “Oh hey Cas, I didn’t see you there. How’ve you been?” 

“I’ve been well. And yourself?” Castiel answered politely, seeming to not be upset at his being ignored. 

“Good. Pretty good actually.” A smile washed over her face as she spoke to Dean again. “I actually met someone.” 

“Excuse me?” Dean asked quickly. “Who?” 

“Before I say anything you need to hand over baby bear, because it’s been nearly six months since I’ve gotten a cuddle from him.” 

“Just don’t wake him or grumpy bear will be spending the night at Auntie Jo-Jo’s.” 

Somehow Dean and Jo managed to successfully transfer the sleeping baby without disturbing him and Jo went on to talk about the new boy she met. His name was Benny and Dean decided to instantly dislike the man until he was able to meet him, though in the back of his mind the Benny guy seemed pretty decent. They spent a long time talking about Jo’s college experiences, and all the interesting things she’d been up to. Castiel seemed genuinely interested in what she had to say making Dean wonder if he and Jo kept in contact after her trip. Dean figured later, when they were alone, he could ask Jo about the guy, find out what he’s really like.

“What about you? Anything new and exciting? Any recent love interests in your life?” Jo asked sarcastically. She didn’t need to ask to know that answer. 

“Totally. You know how the dating world is, everyone’s lining up to get at the single guy with the kid.” He meant it to be a joke but couldn’t help but glance at Castiel who looked at Dean with confusion painting his face before Dean swiftly looked away. 

Jo gave him an encouraging smile nonetheless. “They should be, because you’re excruciatingly perfect. I kind of hate you for it.” 

Deal looked over at Jo who shifted Sam a little, causing the baby to squirm uncomfortably. Dean hoped that he’d go back to sleep because that ‘nap’ had not nearly been long enough for him to come out on the pleasant side. He probably should have taken him inside to take a nap away from a dozen people chatting, but what could he do now? 

Sammy’s little eyes could barely open but he tried to peer up at who was holding him. “De?” 

Jo looked like her heart had just exploded from sheer cuteness as she comfortingly rocked him and whispered, “Shh. It’s Auntie Jo-Jo. Go back to sleep.” 

Sammy made a contented sigh but reached his hand out towards Dean who he had spotted. When Dean grabbed Sammy’s hand the little boy snuggled back down on Jo’s shoulder and closed his eyes immediately, not letting go of Dean’s hand. 

“I don’t know how you don’t just spend all day long cuddling this little man. I swear he is the cutest baby to ever live. Almost makes me want one of my own.” Jo commented dreamily. Dean had to admit, Sammy was the cutest kid he’d ever seen, and he was certain that he wasn’t being bias. 

“Don’t you dare be getting any thoughts Joanna Beth! I’m not becoming a grandmother at this age.” Ellen chimed from a few seats over shocking both Jo and Dean.

Both of them laughed as quietly as they could to keep from waking Sam. 

“Coming from the woman who decided Sam would call her Grandma the moment I signed those adoption papers.” Dean sassed back with a wink. 

Bobby, Ellen, and Dean had decided together that they wanted to give Sam as normal of a life as possible, despite the circumstances, and normal kids had people to call Grandma and Grandpa. It had been their idea, and the two of them had made sure with Dean that he was comfortable with Sammy referring to them as such. Dean had told him that he honestly could not think of any other role he’d want them to have in the kid’s life. 

“Oh you shush, mister, or I’m going to refuse feeding you every Sunday like I have the past few years. It’s not like you exactly _chose_ to take on the responsibility of a parent for your baby brother. But if either you or Jo decide to create another human any time soon, I’ll kill you.” 

“Whatever you say, Granny.” Dean mocked once more. 

“I hate you.” Ellen glared back, trying to stifle her laugh. 

“I love you too Ellen.” 

About an hour or so more went on with Jo catching up with everyone and telling them about her college adventures. Much to his dismay, she seemed to have noticed Dean and Castiel talking alone earlier and was furtively attempting to engage both in conversation with each other when she wasn’t talking with some of her other friends. Through her attempts, he did manage to learn more about the other guy like his ability to speak Spanish, Italian, and French, and how he'd ran three marathons in his lifetime and planned on running one in every state if he could manage it. Dean found that he _liked_ the guy, but though Jo's motives were pure in trying to get them to talk, Dean couldn’t get it out of his head that he was wasting Castiel’s time now that he’d seen how off put Castiel was finding out about Sam. Still, he and Castiel were cordial, both contributing to the conversation when necessary. It wasn’t exactly where Dean had hoped his conversation with Castiel would have gone, but there wasn’t much he could do about it.

After an hour or so Sammy woke up from his nap and Dean took him into the house to go to the bathroom and grab some lunch. He also wanted a moment to get away from attempting to sound cheerful while talking to Castiel. It sucked that he'd never get a chance to get to know the guy as anything more than a friend, that is if Castiel decided to show up at anymore of their family gatherings. He just wished that having a kid didn't make him instantly on everyone's blacklist. He wanted a dating life back, yeah, but what he really wanted was a partner. But he was young and most people he met were young too, no one was at that stage in their life where a kid sounded like a fun idea. 

If Dean were being honest, he had been somewhat promiscuous in high school and college. Not unsafe and uncaring, but Dean knew how to have some fun. He’d like to say that it all came to a screeching halt the moment he became responsible for Sam, but he had tried to keep up with his lifestyle at least for the first few months. Eventually it had just gotten tedious to try and keep such a big secret from people, never bringing them back to his house, never getting to know people deeper than their first names and Dean found himself wanting more. So he tried to go on honest to goodness dates, but every time Sam came up in conversation, Dean was left behind before first base was even in his line of sight. When he realized he didn’t have the heart for one-night stands anymore, and didn’t have the time for dating, Dean had thrown his hands up and told himself ‘if it happens, it happens.’ So far that method had proven to only leave him in a nearly year and half long dry spell. But he'd rather be alone than bring people in and out of Sam's life who wouldn't actually stay. No matter what Sam's wellbeing came first. 

He'd never regret it, taking Sam in, no matter how hard the days got or how much he thought he was failing Sam as a parent. He loved the kid more than anything in the world, it was just hard not having someone he could lean on in his day to day life. Yes he had Bobby, Ellen, and Jo but there was something about having the affection and comfort of a lover that Dean craved. He'd just have to settle with his rag-tag family being enough.

Enraptured in his own thoughts, Dean didn't notice that Castiel had walked through the back door into the kitchen until Dean's had turned around with the two sandwiches in his hand he'd made for him and Sam. Dean eyed the other man warily and Castiel swayed awkwardly in his spot, as if contemplating what to say. “I was wondering if you needed any assistance.” 

“Nope, we’re good.” Dean replied with a tight-lipped smile. He turned his attention to Sam when Castiel didn’t make a move to say anything else. “Sammy, do you want chips or carrots?” 

“Carrots please.” The three-year-old responded politely, just the way Dean taught him.

Dean handed the plate to Sam to hold and placed a hand full of carrots on the plate before searching the fridge for anything the boy liked. “Do you want any watermelon?” 

Sammy’s eyes lit up at the suggestion. “Yes please.” 

Despite Castiel still awkwardly standing in the kitchen, Dean couldn’t help but smile at Sammy’s happy little smile. A far cry from his behavior that morning. “Good choice.” 

Before Dean could grab their plates and head outback, Castiel seemed to have found his voice. “So uhm… So, Sammy is actually your brother. I thought you said he’s your son?” 

Having to fight the urge to roll his eyes, because what did this guy even care, Dean responded, “He is. Legally, he’s mine. Genetically, he’s my brother.” 

“I don’t understand.” Castiel eyes were narrowed and his head tilted to the side like he was trying to decipher the book of life. 

This time Dean did roll his eyes. “What don’t you get? It’s simple. I adopted my brother. My brother is now legally my son.” 

“But why? What happened to your parents?” 

Dean didn’t get why this guy was suddenly so interested in his backstory when earlier he’d seemed so disappointed to find out Dean had a kid. 

“It’s none of your damn business.” Dean shot back. And maybe he didn’t need to be as rude as he was in his response, he’ll admit, but now Castiel was just wasting both of their time.

Those same blue eyes that Dean had found so enrapturing before now looked sullen, almost. 

“Yes, I know that, and I’m sorry for insinuating that it was. I’d just like to get to know you still, and this seems like a big part of your life. I thought we were getting on nicely earlier and I’d really like that to continue.” It seemed sincere enough but Dean had been down that road before: A guy says he’s interested long enough to get what he wants then is out of there like a bat out of hell. He wanted to trust that those shining blue eyes were as sincere as they looked but Dean had himself and his kid to protect. 

“Yeah well, I don’t make it a point to spill the details of my past with guys who have no intention of sticking around longer than one good roll in the sack. So if you’d excuse me, I’m going to take my kid out back to eat lunch and spend time with our family before leaving.”

“Dean, I fear you misunderstand my intentions. I genuinely want to get to know you.” Castiel said, trying to stop Dean from walking out back. If there is one thing that Dean knows to be true, it’s that he’s one stubborn son of a bitch, and even though a part of him wanted to believe Castiel was being genuine, a larger part of him didn’t want to take a chance that he was wrong. 

“Thanks, but I’m not interested. Come on Sammy, let’s go eat.” Dean didn’t care that Castiel’s looked suddenly dejected. Nope, he didn’t think anything of that at all. It didn’t mean anything, because Castiel wasn’t actually interested in Dean. There's no way he could be. What young and educated person wanted to date a guy with a mechanic job and a kid? None, that's who. 

Dean couldn't bring himself to look back as he and Sammy joined the rest of the family at the tables. Eventually Castiel had found his way out too but sat the furthest away from Dean as he could get. Of course Jo instantly took notice in the change of seating and eyed Dean questioningly but he just shrugged in shoulders in his way to tell her they’d talk about it later. He spent the rest of the afternoon chatting with family and putting on a happy face and all in all it was a good night. 

But deep down Dean couldn’t help but wonder if he’d ever meet someone who would embrace that Dean had Sam in his life, and wouldn’t run out on him just because it wasn’t an ideal situation. Even if he didn’t, he knew he still had a good life going for him, and a great kid, and that was worth it for him at the end of the day. Or so he told himself.

**Notes for the Chapter:**

> Swore to myself I wouldn't write a Destiel fic... Didn't think I could write anything remotely as good as all the others but this just would NOT leave me alone! 
> 
> I plan for this to be only 4 chapters long, so if you liked what you read, please tell me! It will encourage me to finish the other ones quicker. :) 
> 
> I do not claim to be a writer, all mistakes are my own, please be gentle with me. <3 
> 
> Thank you for reading this!!


	2. Chapter 2

**Notes for the Chapter:**

> This chapter contains references to Mary and John's deaths. Please read the warnings in the bottom notes if you'd like to know where this happens in the chapter to avoid reading. Thank you <3

Dean decided to stay the night at Bobby and Ellen’s when the sun had completely set and Sammy was out for the count, besides, it allowed Jo and him time to really get to talking. The two of them had known each other their whole lives. John and Bobby had been friends in high school, and remained close over the years. The older men had been in each other’s weddings and it had been Bobby who wrote and delivered John’s eulogy at his funeral. Needless to say, with the two men being so close the Winchester and Singer-Harvelle families grew up like one large extended family. 

Dean and Jo had practically been potty trained together, learned how to ride a bike at the same time, went to the same schools together, shared the same group of friends, and had a countless amount of sleepovers at each other’s houses. It was Ellen who drove Dean to the ER when he’d broken his arm for the first time. It was Mary who Jo went to nervously when she’d had her first period. It was John who told Dean he and Jo couldn’t share a bed for their sleepovers anymore. It was Bobby who awkwardly sat the two kids down and gave them the birds and the bee’s talk. It was Jo who convinced Dean, at the age of 15 that their families would still love him no matter what, that he mustered up the strength to tell them he did not feel anything romantically towards girls. 

And thus Jo got to flaunt her openly gay best friend, and their sleepovers returned to normal. 

It was laying in Jo’s too small double bed, huddled under piles of covers, hidden away from prying eyes that Dean and Jo let out all their deepest secrets and repressed emotions. Jo, though better at expressing her thoughts and feelings than Dean, very much liked people to think she held herself better together than she did. And Dean, well Dean was just allergic to any sort of emotional outburst. Except for at Jo’s. The only place he’d been able to deal with the aftermath of his first heartbreak, and the only place (and time) he’d felt safe enough to breakdown over the loss of his parents. 

So it was only fitting that that’s where the two of them found themselves discussing the past few months apart from each other. She’d finally opened up about all the trials she’d faced in her first year. Homesickness was a primary one, but she didn’t realize how isolated she’d feel being a freshman at 22 years old. She’d taken a few years off after graduating high school to save up some money and travel around the States, but she’d always known she wanted to go to college and pursue something with the environment. She told Dean about how she’d found a small group of friends but she just couldn’t connect with them the same way she had with people back home, and it had left her feeling a little unmotivated. Still she persevered, but was a little wary about how the following year would go. 

Dean tried to fight off the small pity party in his mind long enough to give her some comforting words. Still, it didn’t stop him from wishing he were able to experience college right along with her. Though he’d have graduated by now if he would have stayed in school, he liked to imagine that if circumstances were different he and Jo would have had the best time in college wreaking havoc on all who crossed their paths. But those thoughts, Dean knew, were for another life, not the one he had currently. 

It’s not that Dean didn’t enjoy his life. He did. He was content with the way things were going. Nothing was how he’d imagined it would be back when he was a naive teenager with his whole future in front of him, but life admittedly could have been worse. He loved his home, he loved his family, he was happy with his job, but even when he reminded himself he had it good, somewhere deep down he just felt there was something missing. 

Now, Dean wasn’t some fairytale loving optimist when it came to life. He didn’t think that every story needed a prince charming to be fulfilling. He knew he didn’t need a significant other to bring him happiness. And he especially knew first hand how love, or love lost, could destroy someone. Despite all that though, he wanted someone to share it all with. It was just harder than he thought it would be, finding the _right_ person. 

Eventually, as he expected it would, the conversation between himself and Jo fell to Castiel. Not one for holding back with his best friend, Dean spared no detail as he recounted his conversations with the other man. His first impression, how easily the conversation seemed to flow, how instantaneously attracted to the man he had been, how he had a flicker of hope that Castiel could be someone he could get to know. Jo, as patient as ever, listened to him without interrupting. Didn’t say a word when Dean explained the scene in the kitchen either. Just listened to Dean get it all out. 

“Are you going to say something?” Dean asked the ceiling when Jo still had not responded after he’d just recounted the _look_ on Castiel’s face when he’d seen Sammy. 

“Do you want me to say something?” She asked in her incredulous tone that told Dean she did not see things from his point of view. 

He rolled his eyes. “Obviously.” 

Jo sat up just enough to look Dean in the eyes. Her eyes were patient, but Dean could see the ‘Dean you’re an idiot’ look behind them. “I know Cas. And he’s a really good guy. Like, Dean, I am talking angel status here. I honestly think he wanted to get to know you. Sam and all.” 

It wasn’t what he wanted to hear. In fact, it was the exact opposite. Groaning, he pulled the covers over his face. “Don’t say that.” 

“Why not?” She attempted to pull the covers down from Dean’s face but he refused like a child. 

“Because then it proves that I was a complete asshole to him.” He replied, voice muffled. And that’s what Dean knew he was. An asshole. Retelling what had happened between him and Castiel had shown Dean that he had no reason to snap like he did. But Dean being Dean couldn’t recall a time when he didn’t instantly assume the worst about someone he was interested in. 

“You were.” Jo confirmed pointedly. “But I get it. You’ve been burned a few times too many, you wouldn’t be you if you completely trusted him the day you met him.” 

Dean stewed in thought for a while before pulling down the covers, enough for his eyes to peek up. Jo was staring at him as if she knew that she’d made him see the light. Brat.

“What do I do?” He asked solemnly, knowing she wouldn’t let him off without at least an apology to the other man. 

Jo shifted back down to lay comfortably on their shared pillow. She patted Dean’s hand next to hers on the cover. “Next time you see him, I’d start with an apology.” 

“You know I suck at those.” 

“I do. But I also know the guy volunteers to read to children on the weekend, and taught for four years in a high needs area just because he wanted to.” She paused to let that sink in. Dean knew he wanted to fix what he had quite possibly already screwed up. He didn’t know the guy well, but as for first impressions, Dean was positive he left a bad one. It was something he had to remedy if Castiel were to start coming to family functions more often. 

“He’s a good guy and you’re kind of the one who screwed up here.” Jo spoke when Dean didn’t. 

“He reads to kids?” It wasn’t so much a question of if he’d heard that fact correctly as it was Dean confirming Jo’s testament to Castiel’s character. 

“And teaches them.” She said with conviction, understanding Dean’s non-verbalized question. 

“Angel status?” 

“Of the freaking Lord.” She laughed knowing Dean was trying to find any fault in her judgment. 

“Invite him to the next shindig.” Dean resigned. The least Dean could do was apologize to the guy. Even if Castiel decided he wasn’t interested in Dean anymore. (If he even was to begin with) But if the guy didn’t want to accept Dean’s apology, it was only right that Dean own up to his asshole tendencies. At least he would have tried.

“Good boy.” Jo said with another pat to Dean’s hand, which made Dean laugh. Still he struggled internally with how he would talk to Castiel again. Dean knew he wasn’t someone that others particularly stuck around for. If Castiel did forgive him, and did end up wanting to get to know Dean more, it wouldn’t be long before the other man realized Dean held few redeeming qualities. 

“Stop that. I can hear your thoughts.” Jo huffed with a nudge to Dean’s side. 

“I’m not doing anything.” 

“I’m betting you’re telling yourself that Cas isn’t interested, that he probably already moved on… blah, blah blah. So stop that.” 

“Jo…” 

“No, don’t ‘Jo’ me. You’re stubborn, and obnoxious, and talk while chewing sometimes, but you’re the most selfless and caring person I know.” 

“Stop.” Dean tried to say sternly. He hated hearing the blatant untruths his family loved to smother him with. Yet they always seemed to try and tell him anyway. 

“No! I’m sick of you always thinking the worst of yourself. You’re pretty great Dean Winchester. Plus you look like an Abercrombie model, which no one with eyes can say is a bad thing. Even if Cas turns out to be a moron and can’t see how incredible you are, trust me, someone will.” 

He didn’t think the words were true but he loved Jo for trying. “You know you’re my favorite person right?” He asked her because damn if it wasn’t true. He got lucky he had a best friend like her. 

“I do.” 

“Good.” He said smiling over at her. He'd never admit it but sometimes he'd find himself choked up thinking about how important she was to him. He'd been through some dark times but Jo had been the one who'd held him through all of it and helped him learn the best way to fight away all his demons. He owed her his life and so much more and he wished he had it in him to actually tell her but he hoped she knew anyway.

It was looking at her then, with her blonde hair floating over the pillow that Dean briefly saw a glimmer of his Mom, just enough that he felt his heart pang in his chest. It happened every so often, her same shade of blonde hair triggering moments of memories. His mom and Jo had always been close, so much so that when they were little Jo use to exclaim that she wanted to be Mary when she grew up. She'd watch Mary do her makeup and hair, she'd ask to help whenever Mary baked pie... Jo had loved her like a second mother and it’d been nearly as painful for Jo to lose both John and Mary as it was for Dean. Both friends never really felt like they’d only had one set of parents. It had always been two sets of parents. Until it wasn’t.

Dean took a moment to reel in his onset of emotions before reluctantly pulling himself from the warmth of Jo’s comforter. “I should probably head over to the other room incase Sammy gets a nightmare and can’t find me.” 

“He still getting those?” She asked through a yawn. 

“Not as often, but enough that we have like four night lights between his room and mine.” 

“Poor thing.” Jo said with a frown. Dean had asked doctors, and anyone with a toddler if it was normal, and all ensured him that it was. But it never failed to be hard for Dean to see his kid in tears every night from something Dean couldn’t control. They were fewer and farther between, but still too frequent for Dean’s liking.

“Good night, brat.” He exclaimed, smacking Jo on the calf as he walked around her bed to her door. 

“Night, ugly.” He heard her call from behind him. 

Dean tried to be as silent as possible, careful not to jostle Sam too much, but the kid had managed to spread eagle across the middle of the queen mattress. Not willing to sleep on a six-inch sliver of the bed, Dean had to move him. As carefully as he could he tried to scoot Sammy to fit in the bed but he wasn’t stealthy enough. 

“De?” The tiny voice asked still half asleep. 

“Yeah bubba, it’s De. Go back to sleep, I’m right here.” With the kid coherent enough to not scare him awake, Dean was able to push him far enough over that he’d have enough room to comfortably slide into the bed, though he knew he’d probably wake up with a face full of baby limbs no matter how much room he gave the kid. 

Through a wide tired yawn, Sam asked, “Story De?” 

He smoothed back Sammy’s long locks, ones he just couldn’t bring himself to get cut. “I already read a story tonight, bub. Go back to sleep.” 

It had been a struggle for Dean to decide what he was going to have Sammy call him when he got older. When he first started taking care of the kid, he’d been adamant that Sam would only ever call him Dean, because Dean was his brother and that was all he would ever be to the kid. But as time went on and Dean realized his parents weren’t going to come back, and everyone who didn’t know him just assumed Sam was Dean’s son. It made him wonder who he even was to Sammy. 

Suddenly, having Sammy call him Dean seemed to diminish the significant role Dean had in the baby’s life, but he couldn’t wrap his head around his baby brother calling him dad. It was an uncomfortable situation where he felt like if he went by ‘Dad’ it would lessen John’s role in Sam’s life, no matter the circumstances and Dean didn’t know how to handle that. Eventually, when Sammy mumbled ‘De’ in attempt to say Dean’s name, it’d stuck. It felt neutral enough that Sam could one day decide for himself what he wanted to call Dean. 

As Sammy fell back asleep Dean leaned over and kissed him on the forehead. “I love you Sammy.” 

No matter what happened in Dean’s life, whether he ended up alone or living happily ever after, one thing he knew would always be true was that the only man he would ever need in his life was the little one who drooled on him in his sleep and relied on Dean for everything. It was enough for Dean to fall asleep peacefully. Sammy didn’t have a single nightmare that night.

* * *

Somehow, Dean woke up more rested than he expected to feel but quickly remembered he was at Ellen and Bobby’s. They were too good to him, he knew, but he thanked God for them every day. As expected he looked over to the opposite side of the bed to find it lacking a wide-awake three-year-old begging for food. He allowed himself the luxury of just laying in bed a few minutes longer, basking in what was his first full night’s rest in a few months. Eventually the smell of bacon was enough to drag him out of bed and down the hall to the kitchen. 

Sammy was standing on a step stool at the counter wielding a spatula bossing his Grandpa around in the kitchen. As stealthy as he could, Dean crept behind Sammy and bombarded him with a few kisses to the cheek making the baby laugh. 

“Good morning buddy.” 

“I helped Grandpa make waffles.” Sammy exclaimed proudly pointing to the mess of flour and batter spread all over the counters. Still, Bobby was smiling proudly at the kid despite the mess.

“Did you help him stir?” Dean asked Sam.

“Yes!” Sammy beamed, a sight Dean would never grow tired of.

“I bet you helped him pour the chocolate chips in didn’t you?” 

“Yes!” 

Dean held his hand up in a high-five. “Good job!” 

“Thank you.” 

Dean didn’t deny the inner glutton in himself and went about preparing himself and Sam a plate of food. It was when he got to the pile of bacon that his stomach gave a hungry growl. 

“Sammy made sure to tell me that we had to make bacon for you.” 

“He did?” Dean asked looking down at Sammy who’d clambered off the step stool to get to the table.

“I did.” The little boy held so much pride his voice that Dean wanted to smother him in hugs again. 

“Thank you Sammy.” 

“I ‘membered you love bacon.” 

“I do love it! It’s my favorite.” 

“Me too,” Sammy said with conviction. 

Eventually Ellen and Jo made their way down to the kitchen and the makeshift family sat themselves around the kitchen table. All had mounds of waffles and bacon on their plates after Sammy had told them he helped make them. Admittedly, and unsurprisingly, they were delicious. 

“Oh my goodness, Sammy these are the best waffles I have ever had. They’re my new favorite now.” Dean exclaimed, looking over at his kid who was smiling happily like it was the best compliment he had ever received. 

“Me too.” Sammy said with a mouthful of waffle. 

* * *

Despite it being summer time nothing really changed in the weeks following. With Jo being home she’d offered to watch Sammy during the day while Dean was at work which, for a whole summer, would save Dean a good deal of money on daycare. Granted Dean loved Pamela, and was grateful that she watched Sam at such a low cost as it was, but it didn’t hurt to have a few extra pennies lying around. Thus Dean’s schedule went on as normally as it always did. Wake up, shower, dress, wake Sammy up, eat breakfast, drop Sammy with Jo, get to work, pick Sammy up, eat dinner, bathe Sammy, read bedtime stories, go to sleep, and repeat. 

Dean had hardly thought back to the barbecue or Castiel for the matter. It wasn’t like he’d forgotten about Castiel, Dean just didn’t have the time to spend daydreaming about the conversation he would have the next time he saw the man. It wasn’t until he showed up to work and a hideous gold Lincoln Continental Mark V was on the lift that he allowed Castiel to cross his mind. For a moment he’d gotten excited about seeing the other man until he realized he still owed the guy an apology. 

Walking into the shop he didn’t see any sign of the blue-eyed man, so he looked to find Bobby instead. 

“What’s that beast doing here?” He asked with an exaggerated look of disgust on his face. 

“Had Cas drop it off this morning. Told him we’d service it.” Bobby said from underneath Jo’s car. 

“So you expect me to work on that hunk of shit?” 

Bobby pulled himself out from under the car to give Dean a non-amused look. “Do you see any other cars around here I need you to work on?” 

“Bobby, this car is a disgrace to this establishment.” Dean joked, just to get under the older man’s skin. 

“Quit your yappin’. Just get it done will you?” 

“Fine.” Dean replied with an exaggerated huff. 

Despite his grunting and groaning Dean worked on the car. Possibly with a bit more care than he would usually do on a routine service. He figured if his apology was shit, at least he’d have taken care of the other man’s car to the best of his ability. 

He found himself mentally rehearsing what he would say to Castiel when he’d come by to pick up the car. It was sooner than he expected to have to spew out an apology but he knew eventually it would happen. But the only thing he could think to say was ‘sorry for being a dick, we good?’ 

He could already feel the smack to the back of his head Jo was going to give him for that. 

Luckily, or unluckily, Castiel never came by to pick up his car. Apparently Jody wasn’t able to drop him off to get it, so he’d just pick it up the following morning. Trying not to be disappointed Dean found Bobby in his office sifting through mounds of paperwork that the guy never seemed to get under control. 

“So what’s the damage?” Bobby asked after he’d explained to Dean, with a knowing smirk, why Castiel wasn’t there yet. 

“I don’t know how he’s been driving this for as long as he has.” Dean exclaimed as he wiped the grease and gunk from his hands. “I doubt he’s had an oil change in the time he’s owned it. Had to give it coolant, power steering, and brake fluid. Gave him new windshield wipers, and rotated the tires too but he’s probably going to have to bring this back soon. His battery should probably have been replaced over a year ago and the cars going to need new shocks soon.” 

“I’ll let him know when he picks it up.” Bobby said with a nod. He made his way out to go check Dean’s assessment of the car, despite Dean having been doing this for years. Seeming to come to the same conclusions as Dean, Bobby looked up at Dean with an amused look. “Did you wash it too?” 

Dean’s cheeks and ears flushed red, “I wash all the cars I work on.” 

“Do you wax them all as well?” 

“I had some extra time on my hands.” Dean tried to shrug. 

“Right.” Bobby mocked, reading into Dean’s extra caretaking more than Dean wished he would. 

“Got something to say?” Dean tried to ask sternly, but it lacked heat. He knew Bobby was just teasing him. 

“No.” The older man replied innocently. He started walking back to his office, pretending to talk to himself. “Now I’m sure it’s nothing more than coincidence that the owner of that car asked if you were working this morning, and you happened to take more care with this car than any other you’ve ever worked on, besides your own.” 

Dean could feel himself blushing like a teenage girl. “Bobby.” 

“Just saying.” Bobby shrugged. In the doorway of his office he finally turned to look at Dean. “Oh. I might have mentioned to him that we we’re having a get together this weekend.” 

“What’d he say?” Dean had to kick himself for sounding too eager but he couldn’t help himself. 

“I’m not your messenger, boy. Just be at my house Saturday.” Bobby remarked before shutting the door to his office. 

Dean wasn’t one to argue with his pseudo-Dad. So, a few days later, Dean found himself back at Bobby and Ellen’s house. He’d shown up a little later than he had intended, due to a potty accident that morning. Though the doctors ensured him that boys learned potty training later than girls, it was still stressful when Sammy just seemed to have more accidents than actually making it to the toilet. Dean was looking forward to the day he didn’t have to clean up another human’s bodily fluids. Until then, he’d resigned that he’d never be anywhere on time. 

Arriving at the house, the first thing Sammy asked for was food. So Dean found himself stuck in the kitchen searching through the fridge since Ellen had already put the food away to keep it from going bad under the intense afternoon summer heat. Dean left Jo in charge of Sam since the two were practically attached at the hip now that she was back in town and watching him every day. It was possible, too, that Dean was partially using the kitchen as a means to escape the inevitable apology he needed to offer to Castiel, who was already lounging around the backyard as Jo had promised he would be. Being the coward that he was, Dean wasn’t exactly able to muster up the courage to offer Castiel a hello, but then again Castiel hadn’t initiated a greeting either. 

Dean found enough food to make a plate for himself and Sam, so he headed out back to grab himself a beer and Sammy a juice from the coolers. As he was digging through to find Sammy’s preferred juice flavor he heard Sammy’s high-pitched scream that made the hairs on the back of his neck stand straight. It was one of those ear-splitting cries that never failed to make Dean’s heart stop. Ones were you wonder how it doesn’t actually hurt when coming out of their tiny little bodies. 

He nearly dropped the beer in his hand the moment he heard it, turning immediately to make his way out towards the heartbreaking sound. Dean spotted Sam instantly almost like a gravitational force honing him in on the exact spot of the kid. Dean almost stopped in his tracks when he noticed Castiel bouncing him in a comforting motion. 

“That hurt a lot didn’t it Sammy? Shh. You’re okay. You’re okay.” Dean heard Castiel murmuring to Sammy who was still screaming out his tears. 

Not really knowing how to process the situation, Dean dumbly outstretched his arms, pulling Sam into them the moment Castiel released him. 

“Hey, hey, hey, I got you baby. Shh. It’s okay.” Dean turned to Castiel who was looking at Sammy with wide concerned eyes. “What happened?” 

“I think he was trying to climb up onto the chair and it flipped back. I tried to get to him sooner but I wasn’t fast enough.” The only reaction Dean had at the moment was anger at the fact that no one had been watching Sam better. 

At that moment Jo came clambering over quickly. “Dean? What’s wrong? Is Sam okay?” 

Not able to reel in his frustration, Dean rounding on Jo with venom in his voice. “You were supposed to be watching him!” 

“I know. I had to go to the bathroom though, I thought there were enough people out here to watch him.” She said, eyes wide and frightened. 

“I asked you to watch out for him. You specifically.” He was practically spitting out the words, not able to reel in his anger, despite Sam being in his presence. 

Jo held up her hands in defense. “Dean, I’m sorry! But he’s a kid, these things happen.” 

“Well you could have prevented it if you just told someone else to watch him instead of assuming they would!’ 

“I’m sorry! Okay? I’ll know better next time.” She looked like she was on the verge of tears and Dean just couldn’t bring himself to care when Sam was still crying into his neck. 

“Like there will be a next time.” Dean mumbled under his breath before turning away from Jo. 

“Come on. I think you’re being a little unreasonable.” 

She tried to pull him back by the arm but he shrugged her off in annoyance. “Just leave me alone right now Jo.” 

Dean knew he wasn’t being rational. He knew Sammy had fallen down on his own watch multiple times but that didn’t change the fact that complete dread had washed over him the moment the heard Sammy crying. He took Sammy out front away from the others so that both Sam and Dean would have the chance to cool down. 

Sam was still whimpering, more from fading adrenaline than actual pain, but it still made Dean’s heart ache from the sound. He heard the front door open and close behind him but didn’t bother looking up to see who it was. He thought if it were Jo he might not be able to hold back from actually yelling at her. Even if his inner voice was screaming at himself for already being such a douche to her in the first place. 

“Is he okay?” Came a raspy, low voice that made Dean look up instantly. He was met with soft blue eyes and a shy smile. 

Dean met Castiel’s smile, though he knew it didn’t reach his eyes. “Yeah, he will be. I think it probably just scared him more than anything.” 

“I’m really sorry I didn’t get to him sooner. I should have looked out for him.” Castiel said, pulling at his fingers nervously. 

“Hey, it’s not your fault. I know these things happens. It just scares the shit out of me.” 

Castiel seemed to take that as an invitation to sit down on the step next to Dean. He took a few moments to adjust himself on the step before speaking again. “I know I shouldn’t speak for her, but I do think Jo is truly sorry.” 

Dean sighed. “I know she is. I just need some time to stop rolling through the ‘what ifs’ in my mind before talking to her.” 

“I understand.” Castiel said with a small nod. 

Neither one of them took the initiative to talk to one another, just sat in comfortable silence. When Sammy was feeling better he rested his head on Dean’s shoulder and stared at Castiel pensively. It was amusing for Dean to watch as neither Castiel nor Sammy looked away from the other person’s glace, as if each were sizing the other up. Eventually a wide smile washed over Sam’s face and he looked up to Dean happily. 

“You feeling better bubba?” 

“Yes.” Sammy said with his smile still bright on his face. It always amazed Dean how resilient kids were. 

Dean noticed Sammy looking back over to Castiel. “You should thank Castiel for helping you when you fell down.” 

“Thank you Casyell.” Sam spoke shyly. 

“You’re very welcome Sammy.” 

“Do you want to go back inside?” Dean asked the toddler. 

“Not yet.” He replied and laid his head back comfortably on Dean’s shoulder. Dean just snuggled him tighter. Again the three of them just fell back into comfortable silence, no one needing or wanting to say much of anything. After a while, a few halted attempts, Dean finally worked up the courage to say what he needed to. “You know, I actually came here to talk to you.” 

“You did?” Castiel sounded shocked. 

“I wanted to apologize to you. I was a complete dick last time.” 

Castiel turned to Dean and spoke quickly. “No. No, I overstepped my boundaries. Sometimes I don’t realize when I am being too forward in conversations and I end up doing more damage than good. I am sorry for upsetting you.” 

“Dude. Stop. I’m the one who is apologizing to you. You have nothing to be sorry for.” Dean said with what he hoped was a kind smile. 

“I’m sorry.” Castiel said once more. 

Dean couldn’t help but laugh. “Stop that. Are we cool?” 

Castiel nodded happily. “We are.” 

They sat there for a few more minutes in silence, just gazing out at the few cars driving in front of the house. Sammy started feeling better enough to slide off of Dean’s lap and start towards the small garden of flowers in Bobby and Ellen’s yard. 

“He really is very adorable.” Castiel mentioned, watching the toddler touch every flower he saw. 

“I think so too.” 

Sammy found a bright blue flower and reached down to pluck it up. He smiled proudly at Dean and walked over to where Castiel and Dean were sitting. Sweetly he handed the flower to Castiel. 

“Is this for me?” Castiel asked surprised taking the flower in his hands as if it were the most precious object he’d ever held. 

“Yes. It’s pretty like your eyes.” 

Dean let out a surprised chuckle. “My kid has better pickup lines than me.” 

Castiel’s smile was wide making his eyes glisten beautifully. “I have to admit, I’ve been won over. Is he always so sweet?” 

Sammy had turned back to go look for more flowers and Dean trailed him with is eyes. “Depends on the day. Sometimes I wonder if he’s legitimately a demon.” 

That made Castiel laugh again. “What’s it like, raising a kid?” 

“Exhausting. Emotionally taxing. Amazing.” Dean huffed out, struggling to find the right words. “I don’t know if I could explain it accurately.” 

“I’m listening if you’d like to try?” Dean couldn’t resist the smile lines around Castiel’s eyes. So Dean told him, to the best of his ability, about the nights that he thought he’d lose his mind because Sammy just wouldn’t sleep. About how he thought once Sammy got older that Dean would finally get more than five hours on interrupted sleep only to be met with a toddler who woke up in the middle of the night for nightmares, needing snacks, and wanting a story read to him at four in the morning.

He told Castiel about the level of neediness that children possess. Always wanting to be close, always wanting to be held, always wanting to play or talk. He talked about how there are some days though when kids don’t want anything to do with you When they wiggle out of your arms, run away because they don’t like what they’ve been told or are just too exhausted. 

“And god, they make you late for everything. I don’t think I’ve been to work, a family function, hell even a date on time since I got custody of him. But I never knew I could love anything so damn much that it makes me physically ache. I just don’t know how he’s turned out so amazing because I sure as hell am a walking mess.” 

Castiel’s full attention was on Dean, and it was surprising to him that someone had just listened to him talk about Sam, someone who wasn’t family. But there was something about Castiel that just made Dean feel like he was... different. 

“Is it hard doing it alone?” He asked Dean. 

Dean gave a small nod then shrugged. “I mean I’m not alone. Not really. Bobby and Ellen are always willing to take him for a night or two if I ever ask. So is Jo when she is around. Really anyone here I know I can call and they’d be more than willing to take him. I just hate being away from him more than one night.” Dean looked over at Sammy who’d now decided that the dirt was a better use of his time than the flowers. “Sometimes it’s overwhelming, and I wonder what it would be like to have a partner to share the burden with. But there aren’t many guys out there willing to shack up at this age with a guy and his kid.” Dean didn’t mean it to sound so self-deprecating, but Castiel didn’t seem to mind. He just looked at Dean with sincerity painted on his features. 

“Some would.” The blue-eyed man said, making Dean’s breath catch slightly. 

Trying not to get his hopes up about the meaning of Castiel’s words, Dean tried to play it off. “Well, they’re few and far between.” 

Castiel sat there for a moment fidgeting with his hands in his lap. It seemed to Dean that he was nervous but Dean didn’t know from what, until Castiel spoke. “Would I be incorrect in assuming that we had connected the other week?” 

Dean sighed in relief knowing he hadn’t been the only one to feel it. He met Castiel’s gaze with an encouraging smile. “No, I thought we did too.”

Before Castiel could say anything in response, the front door opened and Dean heard Jo’s timid voice. “Dean? Can we talk?” 

“Auntie Jo-Jo!” Sammy shrieked from his spot in the dirt. He stood up and ran over to Jo who bent down and hugged him tight. 

“Hey baby bear, are you okay?” 

“Yeah! Do you want a flower?” He asked excitedly. 

“I would love a flower.” Jo said down to the little boy who ran back to the flowerbed. She turned to Dean immediately after. “Dean, I’m really sorry about what happened.” 

“I know.” He said softly. He’d long forgotten his anger towards her. 

“I didn’t think that he would get hurt.” She said with tears brimming in her eyes, looking more like a wounded puppy than the strong woman Dean knew she was. 

He pulled her down to his right on the step and wrapped her into a hug, not wanting her to cry over something that had happened to him countless times. “I know you didn’t.” 

“I should have been watching him.” She said with a quivering voice. 

“What’s done is done. And I’m sorry I yelled at you.” He added a kiss to her forehead to let her know he meant it. The two of them never stayed upset with each other for long. 

“Are we okay?” She asked quietly still leaning against his shoulder. 

“Of course.” 

“Here!” Sammy said handing Jo a small yellow flower, ending hers and Dean’s conversation. 

“It’s so beautiful.” Jo remarked while putting the flower behind her ear. 

“Can we go play Auntie?” 

Jo looked over at Dean. “If it’s alright with De.” 

Sammy looked over at Dean with big pleading eyes. “De can I play with Auntie, please?”

“Course you can.” Dean looked at Jo and told her with his eyes that he really was fine with her watching Sam. At the end of the day he knew she’d lay her life down for Sam’s. What had happened in the backyard was just an accident that happens to all kids. Jo seemed grateful for Dean's forgiveness and only then seemed to have noticed that she'd interrupted the conversation between Dean and Cas. Quickly she stood and guided Sam back to the front door before looking over her shoulder and giving Dean an encouraging wink. Dean fought off his blush. He turned his attention back to Castiel the second the door shut. 

“Sorry about that.” 

“Don’t be. I understand.” 

“Where were we?” 

Castiel had a shy smile. “Just talking about how I thought we’d connected until you seemed angry with me and left.” 

Dean closed his eyes and nodded. He was such an ass that day. “Yeah, I’m sorry about that. It’s just the way you looked when you saw Sam was pretty similar to, well, pretty much everyone I’ve tried to get to know. 

“I apologize for it seeming that way to you, but I promise my interest in you was not deterred by finding out about him.” 

“The look on your face said otherwise.” Dean knew he probably sounded petulant, but he needed to know just how Castiel felt about Sam before pursuing the other man. If Castiel wasn’t on board entirely with Sam, Dean wasn’t going to waste his time. 

“May I be honest?” Castiel asked. 

“Of course.” 

“I was having a difficult time reading your signals. I’d spent much of our conversation trying to determine if you were even interested in men. When I thought I figured it out, Sam came along and then you said he was your kid. And I thought, ‘well that answers it, he is interested in women.’”

Dean couldn’t help but laugh. “For the record, I’m not. At all.” 

“I’m not exactly gifted at reading people, and I can’t always tell these things. It wouldn’t have been the first time I mistook someone’s attempts at being my friend as flirtation. Then you confirmed to Jo that you were ‘batting for the other team’ and it made you having Sam even more confusing to me. When you said Sam was actually your brother, I swore my mind couldn’t handle trying to fit all the puzzle pieces together. I didn’t mean for that to come off as disinterest.”

Looking at it from Castiel’s point of view, the whole conversation now made more sense to Dean. He felt guilty that he’d jumped to conclusions, but was thankful he was getting a second chance. Or so he hoped. 

“If we’re being honest here Castiel, I was trying my best to send out _all_ the signals. But I’m a little rusty in that department.” 

“I am as well.” Castiel fiddled with his hands again before looking at Dean nervously. “Dean?” 

“Yeah?” 

“Would you like to have dinner with me Friday night?” 

Dean couldn’t reel in his goofy smile. “Yeah. Yeah, I’d love to.” 

“Really?” Castiel asked, almost shocked by Dean’s answer. 

“Definitely.” Dean assured. 

“Oh, and Dean?” 

“Yeah?” 

“You can call me Cas. Most people do.” 

Dean didn’t know if he stopped smiling the rest of the night. 

* * *

Dean spent the whole week on a high. After leaving Bobby and Ellen’s that night, eagerly, he’d called his sitter and made sure she’d be able to watch Sammy the following Friday night. Dean didn’t know how to explain why a first date with someone he’d only really spoken to a few times left him feeling so giddy, but it did. He’d been smiling so much that even Bobby had to ask if he was on something or not, since it was mildly out of Dean’s character to be so damn happy. The only thing that would have made him happier would have been to see Castiel sometime before the date. They had exchanged numbers, and had texted during the week, but busy schedules didn’t grant either man enough idle time to reply back to the other’s messages. Still the conversations they did have about movies, music, and TV shows left Dean more excited to get to know Cas over dinner. He already seemed to be interested in many of the things Dean was, aside from cars that is.

Friday came around and Dean spent the day with a hoard of butterflies in his stomach. Not once in his life had Dean ever been nervous to go on a date with someone. He’d always been confident, he’d always been sure of himself. Even when he was striking out left and right, he’d gone in to dates self-assured. But this… this felt different to him. This was a night he wanted to work out. This was a guy he wanted to impress. 

He’d gotten home earlier than usual, after annoying Bobby with his nervous jitters. The older man had kicked him out with a ‘take a shower before you scare him off.’ Dean had some time to play with Sammy and wear him out so he’d take a nap before spending a few hours with the sitter. Once the kid was down for the count Dean went about showering, shaving, and getting dressed. 

It was while he was throwing together an outfit that didn’t scream ‘desperate’ (as Jo called the first two he’d text her a picture of) that he heard his phone ring. He hated that his first thought was that it was Cas calling to cancel. But with his luck, it wouldn’t surprise him if Cas decided he didn’t want to go through with a date.

Instead when he picked up the phone Dean saw his sitter’s name on the screen and hesitantly picked up, feeling his heart sink a little when the girl on the other end spoke. 

“Yeah, Becky I understand. No I’m not upset. It’s not like you chose to get food poisoning. Feel better okay kiddo?” 

Instantly Dean felt his good mood deflate. It was ridiculous that he had gotten as worked up about first date as he did. He just hoped when he called Cas that it wouldn’t upset the other man who’d already made plans for the night. 

Nervously he called Cas to ask him to reschedule. 

“Hello?” A deep voice answered sending Dean’s butterflies aflutter. 

“Hey Cas. I know this is going to sound like a fake excuse, but my sitter got food poisoning and I don’t think I’m going to be able to find someone to watch Sammy on a Friday night this last minute. So do you think we could postpone until next week?” 

“Why postpone? We’ll just take Sam along with us.” Cas responded without pause, like it was the most obvious suggestion. 

“No man, I wouldn’t ask that of you.” 

“Dean, I don’t mind really. But I will say I’m not sure what type of things would entertain a three year old. Can he sit through a movie?” 

“Yeah he absolutely loves the movies.” Dean answered, though his own voice sounded unsure. He didn’t think Castiel really meant what he was suggesting. 

“There’s that new Disney one out. You think he’d want to see that?” 

“He would.” 

“Should we grab food before or after the movie?” 

“Probably before. He gets crabby.” 

Dean could practically hear the smile in Cas’s voice, which gave Dean pause. “Where’s your favorite place to go with him then?” Cas asked.

“He really likes Olive Garden right now.” Dean supplied. 

“What a coincidence. I love Olive Garden.” 

Dean thought Cas had to be just trying to impress him, because no one in his or her right mind would want to go on a first date with a three-year-old. “Cas, you really don’t have to do this. We can just go next week.” 

Dean heard Cas sigh on the other line. “Dean, I don’t know how else to spell it out for you. I want to date you. I am fully aware Sammy is a part of that deal, and I want to get to know him just as much as I want to get to know you. I’m glad that he’ll be going with us tonight. Truly.” 

Dean didn’t know how to respond to that, not with the way it made his heart feel warm and gooey in the most chick flick way ever. “Alright.” Dean finally replied. “He’s napping right now. Should be up in an hour or so.” 

“Would it be alright if I came by now?” Cas asked. 

“If you want to.” 

Dean could hear the other man’s smile as he spoke. “I do.” 

Dean spent the next twenty or so minutes scrambling around his house to make it look less lived in by a toddler. For the most part Dean was a tidy person, but taking care of Sammy somehow left him unable to keep anything clean for longer than twenty minutes. The only room in their home that was always clean was the kitchen. 

Right when the living room looked less like a tornado went off in it, there was a knock at the front door. Dean smiled to himself wondering if Castiel remembered to knock since Sam was napping, because most people weren’t that considerate. Dean opened the front door and was greeted with a smile. 

“Hello, Dean.” 

“Hey Cas. Come in.” Dean had to pry his eyes away from the sight in front of him. Dark washed jeans and a deep blue button up rolled up passed his forearms. Dean’s brain practically short-circuited as Castiel walked inside and Dean caught a glimpse of his backside. (Had he mentioned it’d been an extremely long time? Sue him). 

“Your home is very beautiful.” Castiel observed as he walked through the house, still decorated the way his mother had left it. 

“Thank you. It was my parents.” 

“Did you grow up here?” Castiel asked looking at the pictures on the wall of the hallway. 

“I did.” Dean confirmed before remembering his manners. “Do you want something to drink?” 

“Water would be nice.” 

“Alright. Make yourself comfortable.” Dean gestured to the living room as he made his way to the kitchen.

Suddenly Dean didn’t know what to do with himself. He’d already spent hours talking to the guy before today on top of the conversations they’d had since then. He knew it was stupid to be flustered now, but he also knew if this night didn’t go well, there probably wouldn’t be another. That thought alone made him anxious. 

He grabbed Castiel a glass of water and set it on the kitchen table before excusing himself to go check on Sammy. 

Sammy was still asleep but Dean could tell by his squirming that he was getting ready to wake up. Softly Dean sat on the bed and ran his fingers through Sammy’s hair that was stuck to his cheeks. He sent up a silent prayer that Sam would wake up in a pleasant mood. 

“Sammy, it’s time to wake up. We’re going to go to a movie.” 

“Movie?” Sammy asked groggily. 

“Yeah. We’re going to go watch a movie and get popcorn. Do you want to go?” 

The little boy’s eyes fluttered open. “Yes.” 

“Then you gotta wake up and go potty. Okay buddy?” 

“Okay De.” 

Dean helped Sammy out of bed and led him to the bathroom before walking back to the kitchen. He figured if Sammy called for help he could go back to help. He felt rude leaving Cas alone in the living room. 

He found Cas staring at pictures on the wall with a smile on his face. “Is this you?” Cas said looking at a picture on the wall of Dean as a high school freshman, braces and all. 

Dean laughed embarrassed. “Unfortunately.” 

He watched as Cas’s eyes flickered from picture to picture before settling on a picture of himself and his parents on Dean’s high school graduation day. 

“Are these your parents?” 

“Yeah.” Dean confirmed. 

Cas smiled at the image. “Your mother is beautiful.” 

“Yeah, she was.” 

“I’m ready for the movie.” Sammy exclaimed at that moment forcing Dean and Cas to look over at him. 

“Do you remember Castiel?” Dean asked the little guy.

“Hi Casyell.” 

“Hello, Sammy.” Cas responded. 

Sammy tilted his head to look at the other man, as if suddenly realizing why he was in their home. “Are you going to the movie with us?” 

“Would that be alright?” Cas asked the little boy politely. 

“Yes.” Sammy replied with a nod before looking at Dean. “Can we go now?”

“Yes, did you use the potty?” Dean mentally kicked himself for using the word ‘potty’ on a first date, but when Cas didn’t snicker, Dean assumed it wasn’t as embarrassing as he thought it was. 

“Yeah.” Sammy confirmed. 

“Good. Then lets go.” 

As the three of them were walking out, Dean turned to Cas. “Is it cool if we take my car? His car seat is already set up.” 

“That’s perfectly fine.” 

So Dean, like the gentleman his Mama raised him to be, opened Castiel’s door before loading Sammy up in the back seat and climbing into the drivers seat. 

“Sammy what song will it be?” Dean looked through the rearview mirror, waiting for the answer he already knew would come. 

“Don’t you cry no more!” 

Dean smiled at Cas’s confused face that quickly turned to understanding when the Kansas song began playing. The drive wasn’t long and therefore Cas and Dean didn’t bother trying to strike up conversation. Both men were too amused by the three year old in the back seat singing his own rendition of the classic rock songs that played. 

When they arrived at the restaurant Dean ran around to the passenger side to let Cas out before getting Sammy out of the car. The three of them made their way inside. Dinner was mostly Sammy telling Castiel about every story he’d ever read and Castiel telling Sammy about the ones he’s read. Every now and then Sam would be distracted with his food or coloring enough to allow Cas and Dean to have a moment of conversation but Sammy was the one who seemed to be running the show. Not that Dean minded, he actually liked witnessing how Cas interacted with Sam. So far, he really liked what he saw. 

When they did get the chance to talk, Dean took it upon himself to ask the other man questions. Slowly, when granted permission by Sam, Dean learned some of the basics about Castiel’s life. He’d tried to start simply, asking about what the other man was like growing up, hobbies, hang outs, and friends. It amused him to no end that Cas claimed to have had an ‘emo’ phase that lasted most of high school. Castiel also told Dean about his best friend Charlie, whom Dean thought sounded like someone he’d definitely like to get to know. 

Eventually Dean asked the more complicated questions (or ones Dean usually tried to avoid answering at all costs) like what Cas’s family is like and his relationship with them. Devoutly religious, large, and mildly dysfunctional were the adjectives Cas used to describe them. He also learned that Castiel was and always had been close with his parents Jimmy and Amelia, and that he considered his sister Claire one of his best friends. 

Though he wanted to ask Cas more questions, wanting to get to know everything he could about the man, they had to wrap up their conversation if they wanted to get to the movie on time. At the theater Dean asserted he pay for tickets, snacks, and drinks since Cas had bought their dinner and Sammy could put down some popcorn. 

Sweetly, Sammy insisted that he sit between both Dean and Cas, having already taken to Cas far quicker than Dean imagined the usually shy boy would. The seating arrangement didn’t aide Dean in his plan to stealthily grab Cas’ hand in the movie, but still, the night was shaping out much better than Dean thought it would. And when Cas peered over Sammy’s head when the credits started to roll and smiled happily at the green-eyed man, Dean felt like he was soaring. 

As they walked back to the car Sammy insisted on holding both their hands, again blocking Dean from being able to make the first move. It was Cas who reached across the front seat of the Impala and took Dean’s hand, once they started on the road back home, lacing their fingers together and making Dean feel like he’d just won the lottery. 

Sammy was passed out in the back seat when they made it back to the house not even twenty minutes later. Dean asked Cas if he wouldn’t mind waiting while Dean took Sammy up to bed before saying their goodnights, but understanding if Cas needed to get home. 

“I’ll wait for you to get him to bed.” Cas affirmed looking almost shy. 

Dean managed to miraculously transfer Sam from the car, to his shoulder, to the bed without Sammy so much as stirring. Dean knew Sam hated going to bed without a few stories, and Dean figured a midnight story session would be in his future, but at the moment all he wanted to do was get back to Castiel. Softly he kissed Sammy’s forehead, turned on the nightlights and made his way quietly out to the living room. 

Cas was in the living room again peering at more pictures on the wall when Dean found him. 

“He never goes down that easily, so I think it’s safe to say that was one hell of a first date for the kid.” Cas looked over his shoulder and smiled happily when he saw Dean. 

“I’ve got to agree. You’ve quite the charmer on your hands.” 

“Learned all his moves from me.” Dean said with mock smugness, flopping down on the couch and gesturing for Cas to join him. 

Castiel sat down on the couch, still a ‘safe’ distance away, but turned his body towards Dean’s. He gave a sly grin in Dean’s direction. “I’m not sure what moves you’re referring to.” 

“Hey, I’ve got moves.” Dean shot back with fake exasperation causing Cas to laugh a warm rich sound. And Dean knew couldn’t bring himself to let the night end, not yet. There was just so much he wanted to learn about Castiel, so much he wanted to share about himself with the other man. So boldly, he asked, “Do you want to see what’s on TV?” 

Cas cocked his head to the side, attempting to look confused but failing at hiding his grin. “Is this one of your moves?” 

“Is that a yes?” 

Cas’s face lit up. “It’s a yes.”

So the two found themselves on the couch with a random show playing in the background. If asked, neither of them could tell you what it was about or if it were even animated or live action. It didn’t matter, though, what show was playing because all that mattered to either man was the person in front of them. 

It was as simple as breathing, getting to know one another. And that’s what they spent the whole night doing. 

They picked up where they left off in the restaurant. Learning about each other’s college experiences, discussing what they each had planned on doing when they were younger. Castiel revealed how his plan had always been to become a writer, but somewhere along the way he was drawn to teaching and couldn’t imagine himself doing anything else. Dean also described how his goal in life had always been to be in the FBI but now, with another person so dependent on him, if given the chance he couldn’t imagine pursuing something quite as dangerous. 

Almost as if Cas could sense Dean’s hesitance, he only sporadically asked personal questions. Piece by piece Dean told stories about Sammy, Jo, Ellen, and Bobby, revealing more and more about his past. 

The question was always there though, hanging in the air. Dean knew he couldn’t avoid it forever, it was just a topic he knew he’d never be able to easily open up about. But Cas had given him time to warm up to that particular part of the conversation, so it didn’t knock Dean too off guard when it came up naturally. 

“What happened? With your parents I mean.” Somehow, though neither man knew how, they’d inched closer and closer to one another until their knees were touching and their hands hand found each other’s on the back of the headrest. 

“It’s a long story.” Dean responded, drawing senseless shapes over the palm of Cas’s hand with his fingertips. 

“I’m all ears.” Cas replied sincerely. 

It took Dean a moment to gather the strength, knowing that the last thing he wanted to do was breakdown and cry on his first date with the guy. He’d told a handful of people what had happened, but no matter how many times he’d said the words he always fumbled with where to begin. 

“I guess… I guess I can start with: I was supposed to be an only child, hence the gigantic age gap. That’s what my parents intended anyway.” 

Dean looked at Cas and saw that he had his undivided attention. Somehow seeing Cas looking at him like his fucked up experience was worth listening to, gave Dean the courage to continue. 

“I grew up begging for brothers and sisters but my parents always claimed that they just wanted me. And we were happy, really happy, the three us of. But when I was nineteen they sat me down and told me I was going to be a big brother. I guess I thought it was weird that there would be such a huge age difference, but my mom seemed excited despite everything.” 

Dean took a moment to collect himself. The next part always was the hardest to speak of, recalling the details felt like living the same day again. And despite the years in between, it was something that Dean knew he’d never completely heal from. 

“Essentially Mom thought her tubes were tied but apparently it was a piss pore job because somehow she’d gotten pregnant. But her age and other factors made it a high-risk pregnancy…. She didn’t seem scared or anything though, her faith was always so resounding that I didn’t even think to worry when she told me that there was risk involved. I think that made it worse in the end, my naivety with how serious things were.” 

Dean couldn’t look at Castiel, but he could feel the other man’s grip tighten. There were tears stinging at his eyes but Dean refused to let them out, breathing in deeply to shoo them away. 

“I’d made it down in time for the birth and things seemed to be going well, Mom was all smiles, Dad and Bobby were cracking jokes, and I was anxiously awaiting meeting the little squirt. And then everything just turned. In the end she didn’t make it out of the delivery room. It was the worst day of my life, but my pain didn’t compare to the way the grief completely consumed my dad. One moment he was the man I’d grown up with and wanted to emulate more than anything… and the next he was someone I didn’t recognize. Her death caused him to completely lose himself. And six months to the day he decided to wrap his car around a pole.” 

Castiel shifted, and Dean could feel a comforting hand now on his knee, but Dean still couldn’t meet the other man’s eyes. “Dean, I’m so sorry.”

Dean shrugged, trying to mask the hurt. “It’s okay. I should have seen it coming, knew he was dealing with it rough. But I mean so was I. She was my mom, you know? My whole world shattered when she died, so I tried to cut my dad out since it hurt too much. I didn’t come home very often, just drowned myself in alcohol and sex. I mean I came home when Bobby would beg me to… I guess I just didn’t really think my dad would ever do what he did. She was his high school sweetheart though, his entire universe, so I guess I can’t blame him.” 

Dean threw his head back against the headrest and ran his hand down his face. Somehow he’d already opened up more than he had to anyone aside from Jo, and now he couldn’t even stop the few traitorous tears from escaping the corners of his eyes. Still, he wanted to tell Castiel more. Because he felt like he could. Because he felt safe enough to. Bravely he opened his eyes and looked at Cas whose eyes were reflecting genuine heartbreak for Dean’s past. 

“You know, the worst part about it all though was that he was so far gone he didn’t even know Sammy was in the house with him. Said it in his letter ‘I’m thankful Sammy is staying with you tonight.’ I’d only ever spent a few weekends with the kid at that point, and never did my dad ask me to keep him for the night. That’s how bad his mind was. My six-month-old baby brother was left alone in the house for five hours as my dad cowardly took the easy way out before anyone had the chance to notify me of what happened to him.”

Dean sighed as he felt fingers thread through his hair in the most comforting way. “I guess the rests really just history.” He continued. “I dropped out of school, moved back home, and was granted guardianship of Sammy. A year or so after everything went down, I had a talk with Bobby and Ellen and decided I might as well just adopt him since I’m going to be the only parent figure he’ll ever know. Maybe if he were older it would have been different. If he had some memory of our parents, but all he’s ever known is me. It just made sense in the end.” 

There was a long pause as Cas let everything Dean had just put out there sink in. Dean almost hoped that Cas didn’t have to say anything. Feared that he had mistaken the empathetic look in Cas’s eyes as pity. Dean had a lot of baggage and just laid it on thick, on his first date with the guy nonetheless. It was enough to make any sane person run for the hills. 

“Dean,” Dean quickly interrupted what Cas was going to say, fearing that the other man would end whatever it was they had. 

“I know. It’s all really fucked up. But it is what it is. And now you know.” 

Cas shook his head. “I just wanted to say that it’s amazing, what you’ve done. I can’t even imagine what you went through losing both your parents in such a short amount of time on top of becoming a father to your own brother. All while still practically a teenager. No one deserves that much pain and responsibility thrown at them, but somehow you’ve pulled through, built a good life for yourself and Sam.” 

Dean shrugged the praise off like it didn’t actually make his heart feel warm. “Yeah, well, it’s what I had to do.” 

Cas shook his head again, pulling on Dean’s hand so that he’d look in Cas’s eyes. “No it’s not. I’ve met your family and I know that Bobby and Ellen wouldn’t have hesitated in taking Sam in if you’d have expressed your desire for a ‘normal’ life. You didn’t have to take on such a huge responsibility, but you chose to anyway. And that says a great deal about the kind of man you are.” 

Dean wanted to say thank you for those words. He wanted to say what it meant to him that the other man was willing to listen to Dean cry like a little bitch. He wanted to tell Cas just how glad he was that he was there with him that night, but Dean was never one for words. 

“Well now that I’ve put a damper on this night…” He’d said instead. 

“You did no such thing. I’m glad you chose to open up to me.” Cas responded with utmost sincerity in his voice. 

“It’s a lot for a first date.” Dean exclaimed. 

Cas looked down at his lap, and Dean swore he saw a faint blush on his cheeks. “If I’m being honest, I feel like this is more our third.” 

“Is that so?” Dean questioned in a seductive tone. His attempt at lightening the mood. 

He could hear Cas’s smile before he saw it. “It is.” 

Boldly, Dean scooted over on the couch until he was pressed up against Cas’s side. He leaned in close, practically whispering in Cas’s ear. “You know that third dates usually entail a little more than just talking on the couch, right?” 

Cas bit his lip and blushed further. “What do you have in mind?” 

Dean placed his forefinger under Cas’s chin and tilted it up until the two were able to lock eyes. “I’m going to kiss you now.” 

He could hear the hitch in Cas’s voice, and he wondered if Cas’s heart was beating as rapidly in his chest as Dean’s was. Dean knew he was bad at words, but he knew he was good at this. Looking into those too blue eyes Dean realized he’d never wanted to kiss someone so much in his life. 

“What are you waiting for?” Cas asked, tilting his head ever so slightly granting Dean permission to seal their lips together in what Dean knew, by the rush of _home_ he felt down to his core, was the beginning. 

Somehow it just fit, Cas being a part of Dean and Sam’s life. The newness of the relationship didn’t seem to matter when both men were so invested in getting to know everything they could about one another. From that first night on, Castiel came around as frequently as he could, always insisting that they take Sam along with them wherever they went. Movies, painting, bowling, golfing, the park, and everything under the sun that Cas and Dean could think of that was kid friendly they went to. 

Everyone in the family fell for Cas quickly as he just seamlessly fit in with the group. Sammy was the first to be won over, lighting up like a Christmas tree every time Cas came around. Jo, who had already loved Cas since she’d gone to Chicago with him, was overjoyed that he and Dean had finally gotten together, always offering to watch Sammy so that the two men would have a night for themselves. Even Ellen and Bobby were smitten with Cas, never failing at finding an opportunity to tell Dean that he needed to make sure to keep this one around. 

As for Dean, he didn’t know how it’d already been five months since they’d gotten together. For the life of him, he couldn’t remember a time, aside from when his parents were alive, when he’d been so completely blissful. Even Sammy seemed happier whenever Cas was around, and that was enough for Dean to know that whatever this was between him and Cas… it was special. Somehow his life had gone from something missing, to him, Sam, and Cas now being seen as a unit. A family perhaps. Or he hoped. 

They were still in the honeymoon phase, so Dean was trying not to get his hopes up that what they had would last. But being with Cas was the first thing in a long time that just made sense in his life. He no longer felt like he was just drifting through his own life because now he felt like he was really living it. Even when Jo went back to start her second year of college, Dean didn’t feel that overwhelming weight of loneliness that he had gotten use to at her departure. Now he had Cas to spend time with and it felt good. It felt right. 

Dean knew he was falling hard and falling fast, and as much as it excited him, it terrified him too. 

“Are you ready for the last story?” Dean asked his toddler who was coming up with every excuse in the book not to fall asleep. 

Dean knew he won the battle when Sammy let out a full body yawn. “Yes please.” The little boy answered. 

Dean pulled out Sammy’s favorite book, the last one they read each night before bed without fail. 

“Once upon a time there was a little girl named Goldilocks….” 

Sammy had heard the story enough times that he could recite it from memory, but he always listened to Dean with rapt attention, chiming in if Dean ever did a voice wrong. It always tugged at Dean’s heart when he thought that one day Sammy might not want Dean to read to him any longer. He just hoped that day was a long ways in the future. 

When the story was finished Dean slid out of Sam’s bed and tucked the little guy in, smoothing back his hair to give him a kiss to the forehead. 

“Good night, buddy. I love you.” 

“I love you more.” Sammy said back, assertively. 

Dean loved bedtime, more than he could put into words, for this part alone. “Not possible. I love you to the moon and back.” 

Sammy thought for a minute, scrunching up his eyes so he could think of a good comeback. Eventually he raised his eyebrows, signaling the thought he’d found the best choice. “I love you to Grandma and Grandpa’s and back.” 

Dean could practically feel his heart grow ten times the size. He never wanted Sammy to grow up. “Wow. That’s so far. Are you sure you love me that much?” 

“Yes. I love you the most.” Said Sammy with a big yawn.

Dean tucked turned on the nightlight and handed Sammy his favorite moose stuffed animal. “Sleep tight.” 

“Night, De.” 

Dean walked into the living room with a wide smile on his face, and was met with his second favorite sight. Cas sitting bundled up on the sofa looking like he just belonged there. 

“How many stories was it tonight?” Cas asked when he spotted Dean. 

Dean nudged Cas’s shoulder to get him to move over enough to let Dean sit down. He pulled Castiel back against his chest, pressing a kiss to the other man’s temple. “Only four.” 

“A man after my own heart.” Cas joked. 

“Hey now. I claimed you first.” 

“And I’m yours.” Cas turned his head enough to slot his lips against Dean’s. 

“Lets keep it that way.” Dean murmured against his boyfriend’s lips. 

Like most nights, they found themselves intermittently watching guilty pleasure TV shows and heatedly making out until they were certain Sammy wasn’t going to wake up from a nightmare. Then they’d find themselves locked in the bedroom trying their damnedest to not wake the toddler. That night was one of the nights that Sammy had woken up from a nightmare, thankfully Dean was able to sooth with only one book and the kid was able to fall back asleep. 

“Where were we?” Dean whispered in Cas’s ear, leaning over the back of the couch after successfully getting Sammy back to sleep. 

“Right here.” Castiel practically purred as he aggressively pulled Dean by the shirt over the back of the couch sealing their lips together. 

This. This was his favorite place to be at the end of a long day. He didn’t know how to explain it, but being with Cas was something couldn’t fathom having lived without, and ever being without again. Dean was never great with words, but actions he could do. And it was through actions that Dean felt he could show Cas just how much he’d come to mean to Dean. Maybe it was the way Castiel felt comfortable showing his feelings towards Dean as well, because he kissed, touched, and made love with equal passion. 

Every moment they spent together was precious to Dean. Every touch shared was a promise that Dean wanted to make good on. Cas seemed to have a gift in making Dean a complete puddle of mush just by one look. He knew just what to do to make Dean weak. Knew just what words to whisper. Knew just the right way to kiss down the column of Dean’s neck to make him shiver. Knew just the right way to trail his hands up Dean’s body to make the green eyed man melt. 

“God, I love you.” Dean gasped against Cas’s lips after he’d trailed his blunt nails up Dean’s body, sending goose bumps all down Dean’s torso. 

Castiel’s breath caught and kisses ceased as he pulled back to look at Dean, eyes wide in what Dean thought was fear. Dean tried to find a way to back peddle. Ran through any way to get out of this situation. He’d wanted to tell Cas how he felt for more than a month now, but he didn’t know just how Cas would react. He knew Cas cared about him, knew that Cas wanted to be with him. Dean just didn’t know if Cas was quite there yet. Clearly he wasn’t. 

Dean had wanted to wait, planned to wait, until he knew for sure, but his traitorous mouth had spoken sooner than it should have. Dean tried to say something, make up an excuse, say that he meant he loved the way Cas kissed, how Cas smelled. Loved the way Cas’s eyes looked at that particular moment. Anything that would stop Cas from saying that he didn’t feel the same way about Dean, yet… or ever. 

He could feel the panic rising in his throat because he knew that he’d just messed up the best thing that had ever happened to him. Dean knew he was difficult to love, knew that Cas was settling for him; knew that falling for Cas was dangerous because it would only be a matter of time before Cas figured out Dean wasn’t capable of being loved. But Dean didn’t have the chance to come up with a lie to fix the situation, because before he could speak, Cas said something that Dean did not expect to hear in response to his confession. Hell, he didn’t expect to hear it ever. Still, it knocked the wind out of him. 

“Marry me.”

**Notes for the Chapter:**

> I don't know how I do it but I always write far more than I ever plan to. This chapter was suppose to be half the length but I got carried away. Hopefully it's worth it! 
> 
> I just want to say OH MY GOODNESS and THANK YOU for how supportive and encouraging you all were on the first chapter. It seriously warmed my heart! I still plan for there to be 2 more parts but they will likely take a few weeks to get up. (My students have testing coming up and then it's the end of the quarter so I have a thousand things to get in order). Anyway, I'd love to hear if you're still liking this! 
> 
>  
> 
> WARNINGS: This chapter contains references to Mary's death by childbirth and John's death by suicide. If you'd like to avoid this, it is the conversation Cas and Dean have on the couch after their first date. Though I don't believe I was explicit in my explanations I still understand these could be difficult subjects to read and I wouldn't want to upset anyone.


	3. Chapter 3

**Notes for the Chapter:**

> Warning, angst ahead. It wasn't my plan but it's what happened. I hope you enjoy.

_Marry me._

“What?” Dean asked in barely a whisper. For a moment he thought he’d imagined those words but Cas was staring at Dean, with his fingertips to his lips, as if he didn’t understand how his mouth had formed what it just had. 

Marry me. Cas had really said it. Cas had told Dean to marry him after Dean had said he loved Cas. After Dean thought he’d screwed everything up with his confession, Cas had gone ahead and asked Dean to marry him. 

And Dean—Dean didn’t know what to do. He loved the guy. He loved him more than he ever thought he’d be capable of in such a short amount of time. He knew beyond a reasonable doubt that Cas was it for him, that Cas would only ever be it for him. But somehow hearing those two words suddenly made Dean question everything. 

Could he marry Cas? 

Every cell in his body was telling him that yes; yes he could marry Cas, that he wanted to marry Cas. But he didn’t think he should. Looking at the other man on the couch, Dean couldn’t deny just how perfect he was. Angel status, as Jo had said, didn’t even come close to describing the way Dean thought of Cas. The man had endless patience, with Dean, with Sam. He never once walked away when Sammy had a tantrum. Never once left Dean’s side when all Dean could do was snap in angry frustration. Sat through hours of Dean watching old western movies that Cas couldn’t care less about. The frustratingly perfect man had even spent a few weekends at the shop just watching Dean do his job. 

Cas was more loving than almost anyone Dean knew too. The way he talked about his students made Dean’s heart melt. The way Cas already knew Ellen and Jo’s favorite flowers to bring to them on their birthdays, or just because. How he’d call his parents and sister at least every other night just to tell them how much he missed them. How he’d spent the anniversary of John’s death by Dean’s side and didn’t once pressure Dean into opening up about his feelings. How Cas always spent the last few minutes before sleep kissing words of praise and adoration into Dean’s skin, when he thought Dean couldn’t hear. 

And Cas was funny in his own dry-humored way. He also paid complete attention to anyone speaking to him. He was fiercely protective of the people he cared about. Even the people he didn’t know, Cas cared about; the man wanted to teach English to children over seas sometime in his future and he volunteered and was active in his desire to fight for the rights of others. Not to mention his passion for protecting the environment. 

He was perfection all wrapped into one tacky trench coat. 

And what did Dean have to offer? He was stubborn, lost his patience at the drop of a dime, always got senselessly angry, didn’t know how to express his feelings, and didn’t have much to offer if way of a future. Dean knew he was the stagnant figure in the story, the one without much development and a complete lack of an arc, because, well, every story needed those filler characters—those stepping stone characters for the others to progress.

Could he subject Cas to a life of nothing special by marrying him? Because that’s what Dean knew he was. He was nothing special. His only redeeming quality, if you asked him, was his kid. 

And god. They were still so young. Dean was barely going to turn twenty-four and Cas had just turned twenty-six. And maybe because a good chunk of Dean’s youth had been stripped from him by his parent’s death, he still didn’t think of himself fully as an adult. Let alone one capable of sustaining a marriage. 

But Cas had asked to marry Dean. Cas hadn’t just said he loved Dean too. He hadn’t rejected Dean like Dean half expected him to. No. Cas had gone and done the one thing that Dean didn’t know would scare the absolute shit out of him. 

And even though Dean loved him, had just _said_ he loved him. Dean knew if he said yes, somewhere down the line Cas would figure out that Dean wasn’t worth the trouble. And losing Cas then would kill him. 

“Dean?” Cas’s voice was cautious, his eyes now shining with what Dean was certain was fear. 

“I…” Dean started then stopped, unsure of where it would go after that. 

Castiel reached out and swiftly grabbed Dean’s hands. He was speaking so fast that Dean could barely make out his mumblings. “Dean, I’m so sorry. I shouldn’t... I wasn’t.... I don’t know what I was thinking. I shouldn’t have said that. I meant—shit. I meant to say I love you too, but that, _that_ came out instead. I, God, Dean. I shouldn’t ha— I’m so sorry. Can… can we just forget?” 

“So you… so you, didn’t mean it?” Dean asked, feeling simultaneous relief and disappointment pooling in his belly. Really he didn’t know what he was feeling. He wished he could go back in time and not tell Cas he loved him, all so they could go back to their blissful honeymoon stage. 

Cas moved forward, cupping Dean’s face in both his palms, almost unsure of where to put his hands. “No! I mean, yes. Of course I meant it. I did. I do. I do mean it. If you want me. To marry me that is.” Cas was sounding panicky and it pained Dean that it was because of him. That if he hadn’t opened up his stupid mouth then none of this would be happening. That Cas wouldn’t have to be panicking over asking Dean to marry him. 

_Marry me._

The thought was terrifying. Making it harder to breath. Dean didn’t know why he was suddenly so terrified. He didn’t understand how he could be so certain of his feelings for Cas but the very thought of marrying the man was making him cower. Even if his soul was screaming yes, his mind was trying to run. But Dean didn’t know how to voice what was swirling through his head. 

“Cas. I don’t…” 

Cas yanked his hands back like he’d been burned and held them up in surrender. “No. Stop… god please don’t say anything. I get it. It’s too soon.” 

“Cas….” Dean’s heart was breaking seeing Cas so frantic, even though he didn’t know what to say. He wanted so badly to say yes, but the words wouldn’t come out. He couldn’t do that to Cas. Cas couldn’t possibly know he wanted to marry Dean after such a short amount of time. 

Cas’s eyes were wide, pleading, and terrified. “Dean, please. I didn’t want to screw this up and I know this screws up everything, but please let’s just forget this happened. Let’s move on. Go back to what we were doing.” 

But the thing was, Dean couldn’t forget. And he knew Castiel well enough to know that Cas couldn’t forget either. It would always be there, lingering between them, burning hot, until Cas decided to poke the flame once more. And it was better…. It had to be better… if Dean didn’t give him the chance to ask again. (If Dean gave Cas the chance to find someone better). 

“I… I think you should go.” Dean managed to say through his muddled thoughts. He could hear Cas’s sharp intake of breath and the sound of his own heart breaking. 

There was a wobble to Cas’s voice. “No. Please, Dean.” 

“I just…. I just need to think. Some time to think.” Dean couldn’t make Cas’s eyes. Couldn’t look anyway but at a pile of Legos Sammy never picked up off the living room floor. 

“Okay… okay. Yeah… I can give you time.” 

Cas was hesitant to move. Dean was hesitant to let him move. Before he got up, Cas leaned forward, careful not to spook Dean and placed a soft kiss to his cheek. 

“I do love you. Very much. So, very much.” He kissed Dean’s cheek again and it took everything in Dean not to yank Cas back in. “I’m sorry if I ruined everything.” 

There was a pause, and Dean knew that Cas was waiting for him to rebuff his apology. Waiting for Dean to say that Cas didn’t ruin everything. And he hadn’t ruined anything… Cas wasn’t the one who ruined this. It was Dean. But Dean couldn’t form words anymore. Without a response from Dean, Cas lifted himself from the couch, leaving Dean to sit in the emptiness. 

He felt the wind knocked from his lungs when he heard the front door latch shut. It was practically instantaneous the regret Dean felt and his choice. And if Dean were a braver man he might have hauled ass right out of that room and stopped Cas from even getting in the car. But deep in the dark parts of his mind he knew letting Cas walk away was the best thing for the angel-like man. 

He stayed on the couch for a few hours, not really having a desire to move or do much of anything. It wasn’t until a pounding migraine behind his eyes took over that he decided to call it a night. Walking down the hall to his room, Dean contemplated pulling Sammy into his bed that night so he wouldn’t have to be alone. 

He decided he deserved it. 

* * *

Monday morning rolled around and Dean actually considered calling in sick. He’d scrolled down to Bobby’s name before remembering Ellen would insist on watching Sammy to let Dean rest, then he’d have Ellen at his doorstep and his family would see how ultimately not sick he actually was. Groaning he tossed his phone, hearing it clatter to the ground, and stared at his ceiling fan the way he had most of the night. He’d hardly gotten an hours worth of sleep. Every time he thought he’d surrender to unconsciousness, he’d remember that, like an idiot he’d let Cas walk out the front door. And then he’d remember why. 

_Marry me._

Dean squeezed his eyes shut and willed that phrase to disappear. Willed Cas to disappear from his mind too because at the moment it hurt too damn much to think about him. He had to keep telling himself it was for the best since every part of him was screaming to run to Cas’s house and beg him to forgive Dean for being such an idiot. 

Nothing could stop him from slugging around that morning. He avoided looking in the mirror at all costs because he knew he probably looked like he’d been hit by a freight train. It nearly wiped all his, already limited, energy out of him to throw his ass into a shower and then into workpants. 

When it came time to rouse Sammy from his sleep, Dean tried to go through the motions of their morning routine for Sammy’s sake. Tried to be more cheerful than he felt, tried to keep the baby’s spirits high even though his were so low. But he knew that his mood was ultimately affecting the toddler who couldn’t help but whine the entire morning. Dean reconsidered calling out sick again. 

He made it through the day though. Somehow. Even if he’d been short with Bobby and brushed off any attempt at the older man’s prying. Even if he ignored every one of Ellen’s phone calls during the day. Even if he refused to look at the slew of texts from Jo. Even if he found himself sitting in his car outside of Sammy’s daycare not willing to get out and be chipper around the other parents when he kind of felt like crying. He somehow still made it through the day. 

It sucked and he didn’t feel an ounce of joy but he figured he’d better get use to that feeling quickly. 

Sammy was in an infinitely better mood after spending the day away from his caretaker. Dean did what he could to ensure that the kid’s mood stayed that way. Though Dean still didn’t feel up for much, he played cars with Sammy on the floor and watched a movie before cooking the three year olds favorite dinner. 

“De, where’s Cas?” Sammy asked as Dean prepared a plate of macaroni and dinosaur chicken nuggets for himself and the little one. 

Dean tried to ignore the sting he felt at the question. “He’s not coming buddy.” 

“Did he forgot it’s dinner time?” 

Dean took a brief moment to collect himself. In such a short amount of time even Sammy had grown accustomed to Cas’s presence. It’d hardly been two months into dating that Cas, without preamble, became a part of the dinner table each night. Suddenly Dean felt like shit for allowing someone to be a part of Sammy’s life before Dean knew it was permanent. (Even if his brain was screaming at him that he _had_ considered it permanent before…)

“No, he didn’t forget. He’s just busy.” Dean replied to the little boy. 

Sammy seemed to contemplate that before shrugging it off. “That’s okay. We wait for him.” 

Dean placed their plates on the table and helped Sammy climb onto his booster seat. “No, we don’t have to wait. He’s not going to be here for dinner. Go ahead and eat.” 

“He coming for dinner tomorrow?” 

“Probably not buddy.” 

Sammy’s eyebrows scrunched together, a sign that he was getting upset. “Why?” 

“He’s busy.” Dean tried to placate. He hoped that Sammy’s toddler brain would quickly move on to a different subject. 

“But I want him to come.” Sammy whined. 

“I know.” 

Sammy crossed his arms stubbornly. “Tell him to come here. We have to have dinner.” 

And how Dean wanted to. The empty seat across from him was practically mocking him, telling him what an fool he was for throwing away such a good thing. 

Dean pushed Sammy’s plate closer to him and gave Sam a pleading look. “Sammy, just eat your food.” 

Sam pushed his plate away from himself angrily. “No! We wait for Cas!” 

“He’s not coming buddy.” 

“Why?” The heartbroken tone in Sam’s voice made this conversation infinitely more painful for Dean. 

“He’s just not.” 

Sammy’s lip began to wobble. “I want him to come.” 

“I do too. But he can’t come. Please just eat your food Sammy.” He couldn’t bring himself to care that he was practically begging the child. 

“No.” Sam replied forcefully. 

“Come on. Your food is getting cold.” 

“No. Tell Cas to come here.” He was using his puppy dog eyes, effectively breaking Dean’s heart into a thousand pieces. 

“I can’t, bubba.” 

And so another tantrum began. And why? Why did it hurt so much more seeing Sammy so distressed over Cas not being around? Why did Sammy’s heartbreak make Dean’s feel so much worse? 

Not exactly knowing what to do, Dean figured he might as well remove Sammy from the kitchen altogether, hoping that his bedroom would calm him down. To add insult to injury, Sammy hit Dean as he tried to pick him up. And if Dean weren’t already feeling like hell he might have been angrier about it. But really, it’s what he felt he deserved, hurting Cas and hurting Sam by his stupid choices. 

“Sammy. Do not hit. It makes me very sad when you hit me.” Dean tried to reason with the three year old who was trying to squirm out of his arms. 

“I want Cas!” Sammy cried with big crocodile tears in his eyes. 

"Me too," And Dean could feel the tears prickling at the corners of his own. Could feel his resolve breaking at the sight of his kid in such distress over this sudden change in their life. But Dean Winchester doesn’t cry. So he forced himself to reel it in, wiping all his energy he already didn’t have to spare. 

He put Sammy in his room and left him to play with his toys and calm down while Dean walked back to his own room, leaving the door cracked in order to hear the kid. Normally Dean wouldn’t leave Sammy alone while so upset, but he’d already determined he was a failure enough as it was, might as well add another bullet to that list. 

It took Sammy about five minutes to stop crying after Dean left him to his own devices, and in that time all Dean did was lay on his back starting at the ceiling fan. His exhaustion must have gotten to him because the next thing he knew his eyes were opening and a small weight was perched against his side, and he could hear the cracking sounds of pages being turned. 

He groggily swiped a hand over his face and turned to see Sammy looking down at a book in his lap whispering the words he’d long ago memorized. 

Dean reached out to push back the hair that had fallen in the kid’s eyes. “Whatcha reading there, buddy?” 

“Goldilocks.” Sammy replied without looking Dean’s way. 

“Will you read it to me?” 

Sammy nodded his head determinedly and started pointing to the words of the well-loved book. “.... Someone has been eating my porridge too, and now it’s all gone!” 

When the story was finished, and Sammy had read it almost completely accurately (more memorized than read), Dean clapped his hands earning a smile from the baby. 

“De, are you still sad?” Sammy asked as he pushed the book away in order to lie down on Dean’s side. 

“A little buddy.” 

Sammy had an ashamed look on his face. “I’m sorry I hit.” 

And if Dean’s heart didn’t just burst by that precious little apology, “Thank you for apologizing.” 

“Will you be happy now?” 

The amount of love he felt for that kid was truly incomprehensible. “Yeah, I’ll try.” 

And if Sammy wanted to crawl on top of Dean and snuggle into him as if he were still a teeny tiny infant, then Dean wasn’t going to stop him. Dean needed it. 

That night Dean fell victim to dreamless sleep that left him feeling almost more exhausted than before he went to bed. He wanted to roll over and try and grab a few more hours but Sammy was beginning to wiggle, and the face of Dean’s alarm clock said they needed to be up in fifteen minutes anyway. 

He turned off his alarm clock before it could wake up his three-year-old prematurely then carefully extracted himself out of tiny octopus arms. He’d hardly moved to stand up when a pissed off blond figure stormed into his room causing him to practically jump ten feet in the air. 

“What the hell did you do?” Jo barked angrily, not noticing the sleeping baby in the bed. Or if she did, she didn’t care. 

“Jesus Christ!” Dean cursed, he could see that Sammy was starting to squirm and if Jo had woken him up Dean was going to be extremely pissed off. More so than he was for her barging into his room at six in the morning. 

“Sammy is sleeping! Living room.” He growled back at her. She turned and stormed out towards the living room, practically leaving angry smoke in her wake. 

“What did you do?” She rounded on Dean the moment he closed his bedroom door behind himself. 

“Nice to see you too Joanna, didn’t know you were coming home so soon. Come on in.” Dean was seething with annoyance. Really, the audacity of that girl to walk into his house unannounced and start accusing him of shit…

There was fire in her eyes. “Oh, piss off Dean. I need to know why I got a call from Jody yesterday saying Cas was a wreck and why I spent all of last night comforting a six-foot drunken mess in a trench coat. What the hell happened between you two?” 

Dean was taken aback, the thought that Cas could be so upset over _him._ He knew Cas had said he loved Dean too, but surely the other man had to know that Dean was nothing to be upset over. Dean wasn't worth that. Cas had to know.

Despite his heart aching for the man he loved, he wasn’t letting up on his bitterness towards his best friend for coming in and yelling at him. “It’s none of your damn business.” 

Jo crowed Dean, poking him in the sternum angrily as she spoke. “Like hell it isn’t! It’s finals week and I had to drive two hours to go comfort your boyfriend who wouldn’t tell me jack shit about what happened. So tell me now so we can fix this and I can make it back for my test tomorrow.” 

Dean shoved passed her and threw himself on the couch petulantly. “You’re wasting your time. Just go, study, and pass your test. I don’t need you trying to fix my shit.” 

“Dean… what happened? You need to talk to me! Cas is heartbroken and I can’t get a word out of him.” Much like his three-year-old tends to do when being scolded, Dean crossed his arms and turned away from his angry friend. “Oh my god. Dean, the silent treatment isn’t going to make me leave. So either fess up or I’m going to park my ass on this couch all day.” 

She made a show of flopping down on the other couch and then staring at Dean in the most unnerving way. And he knew he was going to crack sooner or later. Dean had a complete inability to keep secrets from that girl. 

“I told him I love him. There. Happy?” 

He watched as Jo’s eyes bugged out of her head. “Holy shit. What?” 

“Yeah.” 

He could see her trying to process that information, knowing just how huge it was that Dean, Emotionally-Constipated, Winchester could have told someone, outside of family, that. 

“Then what the hell happened? Why aren’t you together right now? Dean that’s huge!” 

He couldn’t meet her eyes. “Because I told him I love him and he… and he asked me to marry him.” 

Jo gasped loudly. “Holy shit. Holy shit…. Holy shit.” 

“Will you stop saying that?” 

“Dean, I don’t understand. Why is he so—oh. Dean, no. Dean… why?” She moved from her and kneeled down in front of him, looking at him with wide pitying eyes. 

“What?” He asked, annoyance thick in his voice. 

“You said no.” 

She tried to grab his hands but he jerked away. “Jo, just leave.” 

“No. We’re talking about this.” 

“Why? What’s the point?”

“I’m your best friend and we talk about things! That’s the point. What happened Dean? I thought everything was going well.” 

“It was. It was perfect.” 

Jo got up from the ground and patted Dean’s outstretched legs to get him to move. He pulled his knees up to his chest, allowing Jo the room to sit in on the couch beside him. She pulled her legs onto the couch, crisscross, and faced Dean. “Then why the hell would you say no? Is it just too soon for you?” 

“I don’t know.” He shrugged. 

“I know you love him. So what? Do you just not want to marry him?” She was using her gentle ‘mom voice’ the one she reserved for talking to animals or people she was attempting to comfort, or Sammy. 

“I do.” 

She rubbed both hands down her face in an irritated manner. “Then I’m not understanding why you’re over here throwing yourself a raging pity party while you let the love of your life agonize over thinking he’d screwed everything up with you.” 

“Everything in my life goes to shit Jo.” 

“Dean…” She tried to argue, reaching her hand out to touch his arm. But Dean wasn’t having it. He pushed off the couch, trying to put enough distance between himself and his overly understanding best friend. 

“No! Everyone I love either leaves or dies. I can’t do that again. I can’t go through that with him. Not with Cas. I can’t lose him too.” 

Jo was on her feet now too, trying to walk up to him like he was a spooked mare. “Pushing him away right now is losing him.” 

“It’s better this way than after we’re married and he decides it’s time to go.” He walked towards the kitchen thinking a beer would be nice—even if it were six in the morning. 

Jo slapped Dean’s hand away as he grabbed the handle of the bottle, shoving herself between him and his second attempt at getting a drink. “Not everyone is going to leave you. What happened to your parents, it’s tragic, and it should never have to happen to anyone ever, but they loved you more than anything Dean.” 

Dean scoffed, and walked away from her yet again. Sitting at the barstool by the counter. “Yeah…” 

“No! I’m not letting you question that love. You were Mary’s whole universe. Dean, she never stopped talking about how proud she was of you. She knew you could do absolutely anything you wanted to do in life. And John… I know, I know you hold a ton of guilt from that. I know you think you could have prevented it and nothing will ever really make that pain go away. But it didn’t mean that he didn’t love you, he was just in too much pain to think rationally.” 

“Please stop.” Dean pleaded as he placed his face in his palms. It was too early for _this_ type of conversation. But Jo wasn’t ever one to back down from an argument or a lecture. 

“And I don’t know who you think keeps leaving in your life.” She continued standing next to Dean now, pulling his hands away from his face. “Friends from high school come and go. All those guys you tried to date were never even right for you in the first place. But now? No one’s leaving you. You have people in your life who haven’t left you and wont leave you. I’m here. Mom and dad are here. The rest of our family is here. You have Sammy too. Why can’t Cas be a part of that too? I see it in his eyes, he’ll never leave you Dean.”

“You don’t know that.” 

“I do know that. Because I’ve seen two incredible love stories in my lifetime and I know it when I see it. And I’m telling you Dean, the way you and Cas look at each other is the way your parents always did. The way my mom and dad do too. You can’t just walk away from something like that.” 

Her rich brown eyes were so sincere, but that didn’t stop the doubt Dean had towards her words. “Jo, it’s only been five months.” 

“And some people know after only a day.” She reasoned. 

“I’m not good for him.” 

“You’re perfect for him.” 

He pushed himself off the stool, annoyed that she was counterattacking all of his arguments. Though her arguments were probably baseless, Dean knew she wouldn’t stop until he relented and told her she was right. He was already too close to cracking and giving up the fight but he couldn’t let himself do that. He wanted Cas to have his best chance at finding someone who wasn’t quite as poisonous and self-loathing as Dean. Cas deserved that. 

What he said next wasn’t his finest argument, but it was what he struggled with the most. “I already love him too much.” 

Dean had made his way back to the couch and Jo didn’t hesitate to follow. 

“How is that a bad thing? I know he feels the same about you. What you two have it’s so good and it could be incredible, but you’re not going to know that unless you take the chance, get over your fears and just love him like you want to.” 

“What if I already screwed this up?” 

“Have you been listening to a word I’ve been saying? Cas is in love with you. Cas wants to marry you. All that needs to happen now is for you to pull your head out of your ass and tell him you want the same things.” 

He shook his head, knowing it couldn’t that simple. “I’m just… scared.” 

“We’re all scared. Life is scary. Love is scary. But if you spend all your time cowering in a corner, it’s just going to make you miserable. Either face your fears or suffer from them.” 

Dean sagged in on himself. “I don’t know if I can.” 

“Well, then you’re not the man I thought you were. So don’t come crying to me when you realize a year or so from now how royally you screwed up your life by not taking a risk here.” She was filled with a mix of anger and annoyance; Dean could hear it in her voice. Not wanting to rile her up further, Dean remained quiet. Eventually Jo decided she’d been defeated this time around and rose from the couch. 

She made it a few steps before stopping and turning around. “Dean?” 

“What?” 

“You’re worth it.” Dean’s eyes flashed up to hers, surprised by her random kindness. “Cas fell in love with you for the same reasons all of us love you. You’re worth so much more than you’ll ever know. And it kills me that you don’t see that.” 

He wanted to say something, how grateful he was to hear her say that, or even rebuff her words, but she’d already turned away from him and headed to the front door. 

Dean didn’t bother calling out of work that day. He knew with Jo being back that she would have told Bobby and Ellen everything, and that being family granted him a pass on playing hooky. Instead he and Sammy stayed in their pajamas all day sitting on the couch, and sometimes playing with some of Sam’s toys. 

Around noon, Dean heard his front door unlock, a few hours past the time he’d predicted Ellen would come in to give him the scolding of his lifetime. To his surprise he saw Bobby walking into the living room. 

The look he gave Dean was stern, but there was no heat behind it. “You could have at least called to tell me you weren’t gonna show.” 

“Figured your daughter would have spared me the hassle.” Dean sassed back. 

“Oh she did. But I was waiting on you to grow a pair and tell me yourself.” 

Dean rolled his eyes. He really wasn’t in the mood to deal with two Singers in one day. “You know what Bobby? The doors over there. Why don’t you let yourself out?” 

“And miss out on watching you eat ho hos while crying over sappy romance movies? Not a chance.” 

Dean had a few choice words in his reserve, but decided it wouldn’t be wise to lash out at the guy. Knew Bobby was only there because Jo probably felt he’d be the best choice in giving Dean a swift kick in the ass. The older man took a seat on the couch and kicked his feet up on the coffee table, content not to speak until spoken to. Dean figured the guy would be there for quite some time because Dean was fresh out of energy to open up. 

Sammy came out of his room from his nap about twenty minutes later; during that time neither Bobby nor Dean had spoken to one another, allowing Dean to watch the (admittedly sappy) movie that was on TV. 

“Grandpa!” Sammy screeched the moment he saw Bobby. 

“Hey baby bear.” Bobby said with upmost fondness, stretching his arms wide for a big toddler hug. 

Once Sammy settled onto Bobby’s lap, he looked over at Dean and then back at Bobby. 

“De is sad.” 

“Why is De sad?” Bobby asked curiously. 

Dean looked over to see Sam bowing his head dejectedly. “I be bad. I hit.” 

Bobby hummed his disapproval, “What did we say about hitting?” 

“It’s not nice to hit. Even when we sad or mad.” 

“Did you say sorry to De?” 

“Yes.” Responded honestly. He hated disappointing Bobby. 

“Did you give him a hug?” Bobby questioned, trying to hide his amusement in Sam’s shame. 

“No. I do that now.” The little boy clambered off of Bobby’s lap and ran over to Dean. He put his chubby arms out in indication that he wanted a hug. Dean was more than happy to oblige. 

“All better?” Sammy asked. Dean couldn’t help but smile. 

“Much. Thank you, bubba.” 

Apparently Bobby took Dean’s smile as a sign to move in for the kill. “Hey Sammy. Could you go pick out some books for Grandpa to read to you? I’ll meet you in your room after I talk to De.” 

“Yeah!” Sam replied excitedly at the sound of ‘books’ and nearly bolted to his bedroom. 

“He’s hitting again?” 

Dean nodded. “That was the first time it’s happened in months.” 

“What happened?” Dean knew this was the catalyst for him opening up to Bobby. He also knew he was being overtly stubborn and would have to tell the man sometime that night, even if he’d rather not. 

“He asked why Cas wasn’t eating dinner with us, and when I told him Cas wasn’t coming he got upset. Hit me when I tried to pick him up.” That tiny olive branch was enough to get Bobby on the intended course of conversation. 

“You want to tell me what happened between you and Cas?” 

“Figured Jo would have already done that for me.” 

“She did. But I also know my daughter has a way of explaining things that make you out to be more of an idiot than you are when she’s pissed at you.” Dean couldn’t help but laugh at that. He knew how true it was, could write a whole book on the times Jo Harvelle-Singer exaggerated the idiotic things Dean had done or said to piss her off. 

Dean knew he couldn’t lie to Bobby now, especially since Jo had probably recounted everything Dean had said early. So Dean just dived right in. “I told Cas I love him and his response was to ask me to marry him. I panicked and told him to leave.” 

“Why?” 

Dean scoffed. Wasn’t that part obvious? “I’m no good for him.” 

“And why do you think that?” Bobby asked, sounding more like he was trying to psychoanalyze Dean than just being a listening ear. 

Dean took the bait though. “Bobby, look at me. I’m a single parent to my brother because my parents both kicked the bucket. I’m working in my pseudo-Dad’s auto shop because I have no other skillsets. I’m living out of my dead parent’s home, sleeping in my old bedroom because I can’t bring myself to move into the master bedroom. I’m even eating leftovers that your wife pawns off on me because I can’t always afford to after paying off all the bills. What do I have to offer the guy?” 

He knew it was self-deprecating. Knew he was being a little too hard on himself, but each and every one of those thoughts had kept him up some point in the time he’d been with Cas. He was practically a man-child masquerading as an adult, pretending to have his shit together, when in reality he was a walking mess. It’s a wonder that Cas was even interested in him to begin with. 

Bobby schooled his expression until it was almost unreadable, a telltale sign that he was feeling more emotional than he was willing to let on. Dean shifted a little under his gaze, trying to prepare himself for whatever wise words Bobby was likely concocting. 

“I’m only going to say this once, so you better listen.” Bobby started and Dean sat up a bit straighter. “I was there when you were born. I was the first person aside from your parents to hold you, and I was the first person you ever pissed on. So I’m telling you, as someone who has always loved you like my own kid, that you’re being an idiot right now.” 

“Bobby…” Dean replied, shocked. 

The older man shook his head, stopping Dean from continuing. “No. Listen here. I know—I know losing your Mama hurt you in a way that I can’t even fathom, and that your father doing what he did has left you with a weight on your shoulders that you were never prepared for. And I’ve watched you, this whole time, step up to the plate no matter what shit has been handed to you. It tore me to pieces to see how vacant your eyes were in that first year. I wanted to do anything and everything I could to take that pain away from you, but you handled it. You took on the responsibility of raising Sammy like it was the simplest thing to do. You asked me for a job with determinedness in your voice that told me you were choosing to give that little kid everything. You came around the family, played your part, and did what everyone expected of you. But not once, not once in those years after losing John and Mary did I see your smile meet your eyes.” 

Dean could feel his bottom lip start to tremble and he wanted to look away, but he couldn’t break Bobby’s intense stare. The older man looked like tears might start pooling in his eyes at any moment. Bobby sniffed back the emotion before continuing. 

“But that boy came along and it was like a light switch went off and suddenly you were that boy that use to run around and light firecrackers under my window at night just to make me shit myself. You were that boy who used to pick flowers for your Mama and Ellen from the backyard. You were that boy that used to climb onto your dad’s shoulders and ask him to jump in the pool with you. And that—that’s how I knew he was right for you. You haven’t been this happy in a very long time. Sammy’s always been a happy boy, but even he has changed for the better since Cas started coming around. All we want for you is to be this happy forever because you should be. You’re young, you have a whole lot of life ahead of you. Why are you wasting it being miserable? 

“But Bobby…” Dean tried to protest but Bobby cut him off. 

“I know it’s scary, Princess, but you had a good thing going for you. Don’t you want to be happy?”

“Of course I do.” 

“Then quit dickin’ around you idjit and apologize to the guy.” 

“I don’t think I can.” Dean responded, sounding more like a child than he wanted to. All these damn family members trying to make him out to be worth something was really starting to screw with his emotions. 

“You can and you will or I’m holding the kid hostage until you do.” Dean saw a small smirk flash on Bobby’s face. He knew just how much Dean hated when Sam wasn’t with him. 

“You’d just be giving me a break from parenting, you know.” He replied, trying to play off Bobby’s threat.

“You say that but I know you. I know you’d go crazy being away from him for more than two nights.” 

“You’re evil.” He was thankful Bobby had lightened the mood. But by the questioning look on Bobby’s face, Dean knew the conversation wasn’t quite over yet. Bobby was going to continue insisting Dean apologize to Cas, and Dean didn’t know if he could. “I just… I just need more time to think about it. What I’ll even say to him.” 

The older man nodded, more like he figured something out than understood where Dean was coming from. “I know I’m not in your shoes, but the way your reacting to his proposal is ridiculous. He didn’t ask you to marry him next week. Hell, boy, you know Ellen and I were engaged for five years and had a kid together before we tied the knot. No one is asking you to rush into anything you’re not ready for and knowing Cas, the guy’d live with an eighty-year engagement if it that was the only commitment you could give him. Don’t muck this up with him.” 

Dean hated that he knew each word Bobby spoke was true. “He’s too good for me.” 

Bobby let out a genuine chuckle. “I agree. But he chose you, and that’s gotta mean something to you.” 

And it did. It meant everything to Dean that Cas would waste his time with him. That Cas even allowed Dean the privilege of the past five months with him. But Dean was a big fat chicken shit and didn’t know how to do anything other than ruin great things in his life, let alone fix the things he’d broken. 

Before Dean could say anything he heard a very impatient ‘Grandpa!’ being yelled from down the hall. 

“Guess that’s my cue to go.” 

“Yup.” Dean chuckled, grateful for Sammy’s timing. 

Bobby got up, but just like his daughter, decided he needed to have the last word. It was eerie how alike the two were sometimes. “Just to be clear, there’s no one I know who deserves to be happy as much as you do. You’ve grown into a great man and I could not be prouder of you and the way you’re raising Sammy. Even if you’re a raging idiot most days.” 

“Yeah, well, I guess you’re alright too.” Dean sassed back, avoiding the praise with humor. 

“Fix this before it’s too late.” Bobby said gruffly before heading down the hall to read to Sammy. 

A few hours later Bobby announced that he’d be taking Sammy for the next few days to give Dean time to sort out his issues. He decided not to argue because with Sammy out of the house he could finally crack into that bourbon that he’d been wanting to. 

The bourbon wound up untouched. 

Dean wound up with six Twinkie wrappers surrounding him and a kink in his neck from sleeping on the couch. 

He can’t say he felt dignified when he woke up. 

He also can’t say that he particularly enjoyed how silent the house was with Sammy being gone. He tried to keep himself busy, despite his lack of desire to do much of anything. But with a toddler not running around making a mess in his wake, Dean figured now would be a good time to catch up on some much needed chores. 

He spent a few hours doing laundry, picking up random toys, vacuuming, dusting, cleaning and putting away dishes, and mopping the floors before he decided enough was enough. He needed to get out of the house or else he was probably going to go crazy. 

Without a destination in mind, he grabbed the keys from the bowl by the front door and hopped into his car and just drove. Despite the wind being quite brisk, Dean had the windows down but the music turned off. He found he wasn’t quite in the mood for any of his well-loved cassettes, and he cringed at the thought of turning on the radio. 

Although he’d had no place in mind, he wound up at the one place deep down he knew he wanted to go. It didn’t surprise him to see only a few other cars parked around, what with it being a Wednesday afternoon. As he got out of the car he chastised himself for not having the forethought to stop for flowers. He carried on towards his destination anyway. 

It never seemed to get easier, no matter how many times he’d seen it, seeing his mother’s name written on the charcoal colored stone. It was a beautiful piece of granite, one in which John had agonized over getting just right, but even so it did nothing to highlight the complete radiance Mary had offered the world and that was downright tragic to Dean. No more so than seeing the dates that were carved under her name, proving that she’d been taken from the world far too soon. 

“I know I haven’t come around in a long time.” Dean started, lowering himself to the ground to sit crisscross in front of her headstone. “And I wish I could say it’s because I’ve been busy or things have just been too chaotic, but the real reason is that I’ve been happy. Or I was…. Maybe it’s backwards that I only ever come here when I’m feeling pretty shitty, but honestly, that’s when I need my mom the most.” 

He looked at the piece of stone, almost willing it to speak back to him, but he knew it never would. “I don’t know how it’s already been so long since you’ve been gone. Sometimes I swear you’re going to walk through the front door and everything will just be the way it’s suppose to be. You’d come home and throw all your store bought food into bowls and pretend you’d made it, and all of us would pretend to believe you, you’d ask me about life in the FBI, I’d probably exaggerate to make myself look cooler, and at the end of the night you’d read Sammy all his favorite bedtime stories and you and I would sneak into the kitchen to eat the pie you secretly bought for the two of us.” 

Dean smiled at the idealist fantasy he’d concocted in his mind every time he found himself missing his mom too severely. 

“I miss you every moment of every day.” He whispered, not wanting to let anyone hear his emotional outburst. “I see you everywhere I go. At the park where we use to ride our bikes. At the movie theater where we would always go when you wanted a mother son day. At Ellen and Bobby’s, sitting on the back porch talking with Ellen about anything under the sun. You’re still so alive in our house too. I swear sometimes I catch a whiff of your perfume, and it almost always brings me to my knees.” 

The tears were pooling in his eyes but this time he did nothing to stop them. “And Sammy, he’s so much like Dad, but he does things that are so like you it makes me want to sob sometimes. The way he can’t stand when any of his food touches each other—something I could never wrap my mind around with you. Or how he sleeps with a million pillows, like you’d drive Dad crazy with. And this kid, Mom, this kid is the most loving person on the planet, he always has to give hugs to anyone who looks sad or does goofy little things to make people laugh.” Dean’s lip was full on trembling now, making it harder and harder to get the words out. “I really think you’d be so proud of him if you could be here. Or I hope you’d be proud of how I’m raising him.”

“God I miss you.” His voice cracked as he said it. He had to take a moment to wipe at his eyes. “I’d give anything to be able to have just one of your hugs… or to have you back for one single minute, to see your smile again or hear you sing. I hate this. I hate not having you around for everything. To watch Sammy grow up. To see all his firsts. To be there to meet the man I’ve completely fallen in love with.” 

The last part came out as a choked sob. “And I have. I’ve met someone. His name’s Castiel and he’s perfect, mom. I think you’d like him even better than you like me. He’s good to me, so good to me. And he’s good to Sammy too. Everyone loves him, even Bobby.

“And you’re probably wondering why the hell I’m sitting here crying like a baby. Or maybe you already know… I don’t know how it works up there. But, he asked me to marry him—Castiel, the man I love asked me to marry him and I panicked. He’s the best thing that has happened to me in so long, but I still ran for the hills the moment he brought up commitment. And I don’t know why I’m broken like this. Why does it scare me so much when it’s what I thought I wanted? When it’s what I know I want? 

“Mom, I love him. I love him so much it hurts. I can’t think of a life without him. I don’t want to think of a life without him. But we’ve only known each other for such a short amount of time. How could it work out?” 

He wanted to believe that the soft breeze that stirred up the loose leaves on the ground was her response to him. Wanted with all his heart to believe that she’d found a way to reach out to him and give him the hug he’d been dying for for years. 

“If you’re listening or if you’re even capable, I just need a sign. I just need you to tell me what I need to do. Because you always knew what to do. You always had the answers and the right things to say when I needed them. And I need them so bad right now.” 

He took a deep breath, trying to calm himself back down before he stood up. 

“I love you.” He said touching the headstone. “And I can’t wait for the day when I get to see you again. Tell dad I said hi.” 

With that he turned back towards the car and headed home. 

The bourbon didn’t even cross his mind, even if he could have used a drink. Instead he made a beeline straight for his bed and collapsed, the tear-fest he’d had earlier whipping him out. 

He fell asleep immediately, but his slumber didn’t last long. When he looked at the clock it showed that he’d only been asleep about four hours, putting him close to eleven thirty at night. Dean tried to will his body to go back to sleep, but it proved futile. His pillows somehow still smelled like Cas and it left him tossing and turning with a burning ache in his heart—in his soul where Cas should be. 

He couldn’t take it anymore. He missed his angel more than he wanted to admit. Missed him more than he thought made sense after only three days apart. He contemplated running over to Cas’s house that moment, banging on his door until the man woke up, and begging for his forgiveness at his doorstep. But Dean heard the pitter-patter of rain beginning to hit his windows, and realize that midnight on a Wednesday night was well past Cas’s teacher-induced bedtime. 

Dean knew he couldn’t stay in bed any longer. He crawled out of his covers and made his way to the living room. The rain was starting to get harder outside, reminding him of the thunderstorms that use to scare him as a child. Knowing exactly what he wanted to spend the night doing, Dean headed over to the old cedar hope chest sitting behind the couch. He removed the framed family pictures from the top before opening it up. 

He had to sift through old baby blankets and photo albums before finding the handful of homemade videos his mother had deemed worthy of protecting in the chest. Dean touched each label carefully, trailing his fingers over his mothers swooping handwriting, before finding the one he was looking for. He smiled bittersweetly down at the one he picked before standing and heading over to the entertainment center to pop it in. A few moments from Dean’s first few days home flickered on the screen before the one Dean had been searching for came on. 

Mary was sitting on the rocking chair looking out at the storm that was beating on the windows, rocking a baby in her arms. Dean could tell she was none the wiser that his father had been recording her. She had a radiant smile on her face, despite the dark circles under her eyes that indicated baby Dean had been keeping her up most of the night. Her mouth was moving but nothing could be heard at first on the video. 

It was soft, almost unnoticeable at first, but Dean knew it was there. He knew because he’d begged her to play this for him so many times when he was little. The rain in the video died down just enough to allow him to hear it. Dean closed his eyes, the moment her voice made its way to his ears.

“…remember to let her into your heart, then you can start….” The rain was heavier now; a contrast to the light rain occurring in the video, and Dean smiled at all his memories of his mother soothing away his fears of thunderstorms. “…don’t be afraid. You were made to go out and get her….” 

He opened his eyes, unable to deny himself the chance to see his mother’s smiling face. He could almost feel the gentle sway of her arms as she rocked him to sleep, or out of a nightmare, or soothed the pain from the knee he’d skidded. Could almost feel her curls cascading over his forehead as she pressed soft kisses to it, making all his nightmares and ouchies go away. 

He didn’t care that he was a nearly twenty four year old man, clinging to the couch cushions, wishing his mom would hold him and tell him what to do. He was rubbing his eyes raw, trying not to cry, because he’d already cried earlier, damnit, he didn’t need to be crying again. 

“Good night Dean, remember angels are watching over you.” He heard his mother on the video say. And that’s when he couldn’t hold back the single tear that escaped the corner of his eye. Mary had always had such a strong belief that angels were watching over their family, told Dean every night when she tucked him into bed. If only she knew the angel that had been sent to Dean, the one he pushed away like the idiot he is.

Dean sat up to grab the remote, wanting to rewind the video and watch it again, probably for the rest of the night, until he fell back asleep. Before he could press play there was a knock, tentative at first, but grew louder. Dean looked at the clock, and saw that it was ten minutes passed midnight. He briefly considered ignoring it, because who could be knocking on his door this late on a Wednesday night, or he guesses Thursday morning now? 

Before he could even get up he heard his phone buzzing on the coffee table, Cas’s name flashing on it, accompanied by another knock at the door. His heart was suddenly in his throat. Without thinking he practically ran to the door. Swinging it open, he saw his angel, phone to his ear, arm held in the hair ready to knock again. He looked like he’d just ran from the car to the door in an attempt to get out of the rain. His trench coat had raindrops on the shoulders and his hair looked a little damp. He looked beautiful, is all Dean could think at the moment. 

“Cas….” Dean gasped out, shocked, and completely overwhelmed with emotion. 

“Hello, Dean.” Cas replied back, uncertainly. 

Dean was at a loss for words, fumbling over each syllable he managed to reply, “What are you doing here?” 

He wanted to reach out and pull Castiel into a hug, kiss him like his life depended on it. But Cas was looking at him like Dean was going to force him to leave at any moment. Cas opened his mouth to say something, but stopped. He did this a few times before he seemed to have gather the nerve to speak. 

“I wanted…. I wanted to come here and say that I was sorry. That I shouldn’t have said what I did. That my mind had gotten the better of me and I just said the first thing I could think of. That I’m sorry for jumping too fast into this and ruining what we had…. But no. I can’t—I can’t say that because I’d be lying.” 

Dean couldn’t understand what exactly Cas was saying. The way it felt to Dean was Cas came to a sudden realization that he didn’t want to fix anything with Dean. That this was the moment Cas was going to let Dean down. Closure if you will. Dean’s jaw tightened as he braced himself for the words he knew he deserved. 

Cas must not have seen the dejected look in Dean’s eyes because he carried on. “Seeing you… Seeing you here. I can’t apologize for what I said. Because… I meant it. I meant all of it.” 

Dean looked to Cas, confusion completely in his eyes. Cas seemed more nervous than before but pressed on. “Being—being with you has been the happiest I’ve felt, ever. You’ve made me feel like I belong somewhere for the first time in my life. Being together has shown me just how much happiness I was missing out on even when I had thought myself happy before. You make me feel valued and desired and important in ways I didn’t know I could feel that way.” 

Dean’s heart was pounding in his chest because it sounded to him like Cas still wanted him. That Dean was somehow lucky enough to have a second chance with him. He wanted to say something or kiss the other man, but Cas was still talking quickly. 

“These past few days have been hell. I’ve felt like a whole part of me has been missing. Dean, you and Sam are the best part of my life. And every day that I get to wake up with you next to me and a three year old kicking me in the back, that day just is immensely better than any of the rest. And I don’t want to miss out of any more of those types of days. So I’m not going to stand here and apologize for falling in love with you. I’m not going to take back what I said. Because this is me. Here. Right now. I’m completely in love with you Dean Winchester, and if you feel even remotely the same, I’m here. I’m yours. Even if you don’t want to marry me today, tomorrow, a year from now, or ever, I want to spend the rest of my life with you, and only you.” 

Cas’s words breathed life back into his soul again. And he knew, deep down, that this night—the rain, the thunder, the video—it was his sign. It was his true angel in the sky watching over him. 

“Ask me.” Dean breathed out, looking into the eyes of his future. 

“What?” Cas questioned sounding stunned by Dean’s response. 

“Ask me again.” Dean repeated. 

Dean smiled the moment realization dawned over Castiel. The other man looked unsure though. “Dean…” 

“Castiel Novak, ask me again or so help me I’m dropping down on one knee and asking you.” 

“You want…?” Cas trailed off but Dean answered the question anyway. 

“You. I want you. And I know I was an idiot and that I will never in my lifetime be good enough for you but I swear to you I will spend an eternity trying to deserve your love.” 

“Dean—“ Said once more and Dean had to hold back a laugh, because he swore that syllable seemed to be Cas’s favorite. 

He rolled his eyes fondly at the blue-eyed man. “Will you just ask me already?” 

“You are infuriating.” Cas said through watery laugh. 

“And you love me because of it.” 

“I do.” Cas stepped forward, cupping Dean’s face between the palms of his hands. The two took a moment to just gaze at each other, relishing in being able to have such a simple touch once more. A small, tender smile, graced Castiel’s lips before he spoke, “Dean Winchester… Will you marry me?” 

“Yes.” Dean barely got his answer out before Cas crushed his lips to Dean’s. It didn’t take long before Dean felt himself being spun around and pinned against the front door. The kiss was equal parts tender and needy. Cas’s whole body was pressed flush up against Dean’s as if he were scared he would disappear. 

“Never do that again.” Cas murmured as he pressed hot opened mouth kisses against Dean’s jaw and down his neck. 

“I promise.” Dean whispered back. “Never. I missed you so damn much. I’m so sorry.” 

“Don’t. Don’t do that.” Cas pulled back to look in Dean’s eyes before shaking his had and diving in for another kiss. 

“I was an idiot though.” Dean gasped against Cas’s lips. 

“I know.” Cas responded with a giggle, nipping gently at Dean’s bottom lip. 

Dean playfully nudged him. “Hey.” 

“You said it, not me.” 

There wasn’t much taking as both men dove in for another kiss, pulling off layers of clothing when they had to come back up for air. Dean was never, never going to let this go again. He was going to make good on his promise to earn Castiel’s love because that man was truly a saint for putting up with all of Dean’s crazy. 

Dean pulled back as they fell onto the bed together, looking into Cas’s eyes. “I love you.” He said, voice sturdy. 

Cas smiled a radiant smile that flooded Dean’s heart with warmth. “I love you too.” 

And the two spent the rest of the night showing each other just how true those words were. 

They were a tangle of limbs when morning rolled around, neither man willing to be more than an inch apart from the other. Dean woke up first as he hoped he would, allowing him the time to just stare at his boyfriends—fiancés—sleeping form. Though he was still scared, everything Cas promised Dean in their private hour of the night made Dean feel more secure that Cas would truly never leave him. 

Dean heard the bedroom door creak open and the soft pitter-patter of tiny feet running towards the bed. Before he knew it a small body jumped on top of him and Cas, effectively waking the other man up. Dean peered out the door to see Jo slowly walking away from dropping Sam off. 

“Cas!” Sammy squealed, too loudly for morning time. 

Cas let out a small, disgruntled groan before opening his eyes and smiling sleepily at the little guy. “Morning, baby bear.” 

“You not busy no more?” Sammy asked, still a little too loud. 

Cas shook the sleep from his brain. “What do you mean?” 

“De said you were busy so you didn’t comed for dinner.” 

Cas looked over at Dean who shrugged, before turning back to Sammy. “I’m not busy anymore, no.” Cas answered. 

“Good. I miss you.” Sam said with a smile, leaning down to wrap his arms around Cas’s neck. 

Cas closed his eyes and smiled contently, and Dean’s heart almost didn’t fit in his chest anymore with how much it swelled at the sight. “I missed you too Sammy.” 

“Will you make happy pancakes?” Sammy asked as he pulled away from the hug. 

“Is that what you’d like for breakfast?” Cas questioned, knowing all too well what Sam’s answer would be. 

“Yeah!” 

“Then I’d be happy to make them for you. Would you like to help?” 

“Yes please.” Neither Cas nor Sam looked back at Dean as they crawled out of bed and headed to the kitchen. Dean just shook his head fondly and watched as the two loves of his life made their way out of the room. He wouldn’t mind having this for the rest of his life, he thought. 

As he could have guessed, all responses to Dean and Cas making up were along the lines of ‘thank god, don’t mess this up again Dean or so help me.’ They were allowed some time away from family to talk through some things, knowing that the insecurities Dean held wouldn’t just go away over night. The two understood that there would be more ups and downs in their life, but both were more than willing to fight for it.

* * *

The little family of three huddled under the makeshift fort they’d constructed in the living room, reading some of Sammy’s stories. Dean was onto his last story of the night, and was adding in voices that made both Cas and Sam laugh. “Someone’s been eating my porridge—“ 

“No!” Sammy said suddenly, pausing Dean in his tracks. 

“What’s wrong?” He asked the little boy. 

Sammy looked at him like the problem was obvious. “Cas is Papa Bear.” 

“Then am I Baby Bear?” Dean asked confused, he’d always read all the parts to Sammy, except when Sammy requested he read along too. 

“No. I Baby Bear!” 

Dean scrunched his eyebrows together. “Then that leaves Mama Bear. Are you trying to tell me I’m Mama Bear?” He wanted to sound more upset than he was, but it was honestly fitting that Sam would make him Mama Bear. 

Sammy shook his head and rolled his eyes at Dean like he was done with him. “No. You Papa Bear too. You other Papa Bear. You Daddy Bear!” 

Dean felt his heart soar. Not once had Sam ever referred to him as his dad, and he’d also claimed Cas as his own too. It was enough to make Dean’s eyes a little watery. “I see what you did there, Baby Bear. Works for me. Does that work for you Cas?” 

Cas’s blue eyes were shining too, and Dean knew how much Sammy’s words had meant to him. He’d already expressed his desire to adopt Sammy after the wedding, a plan in which Dean was more than happy to agree to. 

“It does.” Cas responded, kissing Sammy’s forehead. 

And everything was how it should be, the missing piece to their life, securely locked into place inside a drooping blanket fort putting on his best Papa Bear voice and continuing the story.

**Notes for the Chapter:**

> I'm sorry for any and all mistakes. I kind of tapped into a very emotional part of myself while writing this, and going back to edit was very hard for me. I just felt like I'd set up a lot of pain in Dean's past that I couldn't just ignore. 
> 
> Let me know if you enjoyed. There will be one more part, the plan is that it will be an epilogue. I've outlined a bit of it but it will still take me a few weeks to get up because I'll be on vacation soon. 
> 
> Again, thank you to all who have read, left kudos, and commented. I am completely floored by kindness I have gotten on this! It's made me so happy. Please share this with others if you know they'd like it too. :) 
> 
> If you're curious my inspiration for the 'home video' scene was inspired by this song: https://www.youtube.com/watch?v=Vgwcu5Qf01E


	4. Chapter 4

**Notes for the Chapter:**

> I cannot put into words how much all your kindness and support for this story has been! Thank you so much for giving this a chance, I truly hope you enjoyed it!

He didn’t know if he was allowed to be as nervous as he felt. He had had months to prepare for this, yet nothing was able to prepare him for how he’d feel on the actual day. He didn’t feel prepared, didn’t think he was going to do well with this massive change to his life. It was at least a blessing that the people who loved him and made him feel secure surrounded him. Yet it meant there were more people around to see him internally freaking out. 

To be honest, he didn’t think to even hope that this day would come. It’d been a long road. There were more ups and downs than he could count, but he’d made it. They’d made it. And it was everything they ever wanted. 

“You okay?” He jumped a little, startled by the sound of another person’s voice. Shaking a smile onto his face, he turned towards the comfortingly familiar voice. 

“Hey Papa Bear.” 

A smile washed over Cas’s face instantly. “You only ever call me that when it’s just the two of us.” 

Sam nodded in agreement, “It might be weird for a grown man to call his dad ‘Papa Bear’ in public.” 

“I don’t think it’s weird.” Cas said truthfully and Sam let out a laugh. 

“That’s because you’re weird.” Sam nudged Cas in the shoulder playfully, and tried to force a smile. He knew it was pointless to pretend that he wasn’t nervous, but he tried anyway. Cas always had the gift of being able to see right through both himself and Dean. 

Cas’s eyes squinted, “How are you feeling?” 

“I don’t know.” Sam said with a shrug. 

“I don’t believe you.” 

“I—I guess….” Sam turned towards Cas, eyes downcast, feeling a lot like a young child than the thirty year old he was. “Would you make fun of me if I said I was scared shitless?” 

Cas waited patiently, as always, for Sam to look him in the eye before speaking. “Of course not. It makes you human.” 

Sam fiddled with his hands, a habit Dean claims he picked up from Cas over the years. “Were you this nervous?” 

“Absolutely.” Cas asserted, causing Sam to look up, shocked. 

“Really?” 

Cas gestured for them to sit down at the chairs next to them, guiding Sam away from nervously people watching out the window. “When I came into your life you were a toddler. Dean had already gone through all the hard stuff before I walked in. So when your sisters were born I felt completely in the dark. I didn’t know if I’d be any good at caring for a newborn at all.” 

Sam had to let out a laugh of disbelief, because the idea of Cas being bad at anything that had to do with family was borderline impossible. “That’s insane because you were awesome at it.” 

Cas’s hand met Sam’s shoulder, a comfort Sam had grown to relish in when offered by either one of his dad’s. “Just as you’re going to be. In all your life, there’s little that you haven’t excelled at, and I know with certainty that this won’t be any different.” 

He’d blame it on the lack of sleep later, but Cas’s confidence in him truly brought tears to his eyes. Though it didn’t make the nerves disappear, he felt a weight being eased off his shoulders. 

Sam sometimes thinks he can remember when Cas came into his and Dean’s life but part of him thinks he made up those memories because of how badly he wishes he could remember. He likes to say he remembers the wedding, just a year and half later of the two men meeting, but that too he thinks he just fabricated. (But he is almost certain that he can remember when he asked Aunt Jo to marry him at their wedding… he probably only remembers that because of the horrifically embarrassing video of the moment that Cas and Dean love to play for anyone in Sam’s life.)

And really, in the long run it didn’t matter if he could remember at the finer details of the beginning of their time as a family because all of it happened anyway, and it brought him to where he is now. One thing Sam knew for certain was that when he looked back on his life he couldn’t remember anything that didn’t feature Cas and Dean, his two greatest heroes, and that was what mattered. 

Growing up for Sam had been great. From an outsiders point of view his life may have been unconventional, but he was always completely happy. Dean never did keep Sam’s true parentage a secret. He had let Sam know about John and Mary’s deaths when Sam was old enough to understand. It didn’t register with Sam how unusual his family situation was, not even when kids at school tried to make fun of him for his two dads; or worse, when people knew his family’s history and made fun of him for having a ‘father-brother’. He had his two dads (and eventually two sisters), his grandparents, his aunt, and the memory of his real parents, all of which just registered to Sam as family—as love. 

And those two dads… He’d never be able to put into words all that they did for him. 

Sam always felt safe and loved. He never once doubted that Dean and Cas’s first priority was always himself and his sisters. He always knew that his dads made sure to include him in all the big moments too, like when they moved out of his childhood home, to one that didn’t harbor the memories of John and Mary; Cas and Dean made sure Sam liked the new house they picked. Or when they went on family vacations around the United States and some foreign counties—ones Cas insisted on to allow Dean to see the places he always dreamed of—they always made sure they were places Sam wanted to see too. And when his dads decided they wanted to extend their family, when Sam was five years old, they made sure it was something Sam wanted as well. 

Sam didn’t know too many parents as thoughtful as the two of them. He didn’t know too many parents who cared as much as his did. The more he looked back on his life, especially at this stage in his own, the more he realized just how incredible both of them were. 

Dean had always encouraged Sam to try anything he had an interest in. He pushed Sam to not give up on anything (that included tuba) until he’d given it his best shot. Cas was the one who who taught Sammy how to ride a bike one summer, never getting frustrated or losing patience when Sam took a while to trust himself without training wheels. Cas and Dean both taught him how to drive a car (though they used Cas’s car for that task because even though he was a cool dad, Dean wasn’t _that_ cool). 

To Sam’s dismay they stayed up like lame parents after his first date, asking him embarrassing questions about if he kissed her goodnight or not... causing the kid to storm up to his room in a fit of teenage hormones. (They did let Sam stay up and wait during both of his sisters first dates, as well as interrogate their dates, so he forgave them for embarrassing him). Unsurprisingly, they also took countless prom pictures, making sure to get the most unflattering pictures of Sam possible, pictures that are now framed and hung on the wall of Cas and Dean’s home to embarrass Sam for eternity. 

There were difficult times too, like any kid has with their parents. Where in hindsight, Sam knew the two of them were looking out for his best interests, but at the time he hadn’t been able to see it. Like when he met a girl name Ruby and started making unwise decisions at school, ditching, not completing work, or being disrespectful. It was Cas who had sat Sam down and scolded him for treating Dean so poorly. Who’d made Sam understand just how much it hurt when Sam, in his teenage rebellion, angry with Dean for asking him to stop seeing Ruby, said things like, ‘you’re not my dad, you’re just my brother.’ Sam remembers those days, knowing that despite how awful he’d been to his dad’s, he never went to bed without hearing them tell him they loved him. 

It wasn’t even just Dean and Cas who were great to him. He had a whole slew of people in his corner: his grandparents, his Aunt Jo, Uncle Ash, and his Aunt Claire too. The whole family amazed him. And it was that whole family, but a little more Cas and Dean, who cheered the loudest in the entire auditorium when Sam was called up for the valedictorian speech as his high school graduation. 

No one allowed Sam’s fears of not getting scholarships deter him from applying to all of his dream colleges. Every person in Sam’s life ensured him that they’d never let him settle for less than his dream school, even if they all had to take out personal loans to make it happen. Sam knew, when he did eventually go to his dream college, Stanford, that he could call each and every one of them when it got too much. And he did. They stayed up on the phone with him late nights when he was freaking out about midterms, finals, and being so far away from home. 

They drove out, caravan style, whenever they could to spend time with Sam, and eventually meet Sam’s girlfriend and later fiancé. But, despite Sam’s absolute love for his entire family, there were times when that large group was just too overwhelming. When Sam needed only his dads…

It was both of them, only Cas and Dean, who’d hopped on a plane the first chance they could (without a thought to Dean’s fear) when Sam lost his fiancé Jess in a fire during college. And though it was Dean that Sam violently clung to as he mourned his first love. It was Cas who said everything Sam needed to hear. 

They never pushed Sam to talk more than he wanted to about his grief. They never forced Sam to reach out to any of his worried family members until he was ready. They stayed with Sam, in California, helping him get back on his feet, and continue in his college career. The two of them never once let Sam feel alone in his loss. 

Eventually, they listened to Sam assert that he was ready to let his dads move back home. And eventually, Cas and Dean welcomed Sam’s late night phone calls again, freaking out over his homework, exams, and later his struggle with finding a job. 

When all wounds had healed, a few years later, his dads were the ones who gently nudged him to try and start dating again. 

He’d have never made it through without them. Would have never made it to where he was, sitting on some fugly waiting room sofa, with a newborn son just down the hall. 

His dads made being parents look effortless. They knew the right times to offer some tough love, and they knew the right times to smother their children with annoyingly suffocating love. They were annoyingly perfect, and he wanted more than anything to be just like them. But Sam didn’t know how he’d ever be half the dad that both of them were to him. 

“Where’s De?” Sam asked, after an unknown amount of time sitting in silent comfort. 

Cas smiled a smile Sam didn’t know if the other man was aware of, a smile that only ever washed over his face at the mention of Dean. It melted Sam’s heart seeing how in love they still were after all that time. “With Sarah. Emma and Alex are with them too.” 

Sam could feel his own smile at the mention of his wife. He’d met Sarah about three years after graduating from Stanford Law at an art auction he’d accidently walked into by mistake when he’d been trying to find his firm’s holiday party. It was, for lack of a better phrase, love at first sight and they were married within the year. 

The family loved her. Dean so much so that he’d told Sammy to marry her the day Sam brought her home to meet the family. She was brilliant, and radiant, and made Sammy feel like the luckiest bastard who ever lived, and he wanted nothing more than to start a family with her. 

And so he did. Two years after marrying the greatest woman on planet earth, his son, Hunter Robert Winchester, came into the world. 

Sam didn’t know how it was possible to love something with such intensity it made him want to cry. Looking down at his child, his son, for the first time was as if every missing piece to his life had somehow come together. He wanted nothing more than to protect that baby and ensure every moment of his life would be filled with happiness. 

It completely terrified him that he’d screw it up. 

After having held his baby for hours, Dean had practically shoved Sam out of the room telling him he needed some time with his grand baby and that Sammy ‘could use some caffeine.’ And that’s how Sam found himself, stewing in his own fears about fatherhood, wondering just how in the hell he would ever be as good to his own kid as his dads were to him. 

“You ready to go back in there?” Cas asked, allowing Sam a few more seconds to stave his nerves. 

Sam smiled at the thought of having his baby in his arms again. “Yeah. I already miss him and I’ve been out here, what? Fifteen minutes?” 

Cas light up with a gummy smile, moving to stand up. “Welcome to fatherhood. Dean never could handle being away from any of you for more than a night. It’d drive him crazy not knowing you were safe in his immediate vicinity.” 

“He was always so funny about that.” Said in reply as the two men made their way down the hallway towards the hospital room. 

The two men stopped at the doorway when they got there and just peered at the scene in front of them. Sarah was talking and laughing with Sam’s sisters, Emma and Alex, while Dean bounced and cooed at Hunter near the window. Sam’s heart practically melted at the sight in front of him. He looked over at Cas to see that he too was mesmerized by the picture in front of him, but Sam knew that his sights were set on Dean. 

Cas’s smile was a little watery as he spoke to Sam in a hushed tone. “He’s looking at him like he always looks at you three. He’s already so in love with that baby.” 

“And that baby is going to be so in love with him. With both of you.” He was tearing up again saying these things to Cas, but he didn’t care, he was filled with far too much love to care if he looked like a fool. He looked at his dad with sincerity in his eyes. “You know you two are going to be the best grandparents in the world, don’t you?” 

“We’re aiming for it.” 

With that, Sam threw himself into a bear hug. He let that hug last even longer than normal before pulling back and wiping at the few tears that managed to escape. “Come on. Sarah’s probably about to send out the sisterly-search team to come bring us back.” 

The two men walked into the room, Sam making a beeline for Sarah and Cas made one towards Dean. 

“Hey beautiful.” Sam whispered as he kissed his wife on the forehead. 

“There you are.” She said with a smile, “I was about to send your sisters to come find you.” 

“Did you bring us back any coffee?” Alex chimed in, looking down at Sam’s coffee-less hands. 

“Didn’t get the chance, Dad and I ended up talking.” 

Both girls nodded their head understandingly before Emma spoke up, “We’re going to go get some then, because we might actually fall asleep on this floor.” 

Sam laughed in response and then stood to give both of his sister’s hugs. 

“You know, I’m so glad Sarah’s genes won this battle or else this kid could have come out looking freaky like you.” Alex teased as she hugged Sam back. 

Sam tugged on the end of her braid playfully, “You know what? I’m going to make sure he prefers Emma as an aunt just because you said that.” 

“He’ll prefer me regardless.” Emma joked. 

Alex punched Sam playfully in the arm. “ But really, you make cute kids, big brother.”

“I agree.” He said with a delighted grin. 

Both his sisters quickly told their dads were they were headed before walking out of the room. In that time, Sam sidled in next to his wife, wrapping an arm around her to pull her close. His dads were standing across the room, still gazing down at the small bundle in their arms, completely oblivious to the world around them. 

“Have I told you how incredible you are?” Sam asked suddenly, looking down at his wife. Even after spending twenty hours in labor she still looked like she could be on the front cover of a magazine. 

She smiled sleepily, “About ten times today.” 

“You just created and brought a human into this world. You’re a superhero.” 

“You helped you know.” Sarah shot back with a playful wink. 

“You did all the hard work. You gave me a son.” 

“He’s pretty perfect isn’t he?” 

“He takes after his mother.” He pressed a gentle kiss to his wife’s lips. He couldn’t believe that this life was all his. He couldn’t imagine feeling happier than in this moment. “I love you.” 

“I love you too.” 

Hunter eventually got hungry and fussy enough that Dean had to give him back to his mother, though it looked like it physically pained him to do so. A few hours later the doctors gave Sarah and Hunter the all clear to go back home. 

Back at Sam and Sarah’s house, everyone was working to clean up the mess that was left when Sarah went into labor during Thanksgiving dinner. Emma and Alex were working to clean the dishes, while Dean was doing the laundry, and Cas was figuring out something for them all to eat for dinner. Sarah was shooed off to the bedroom to get some much-needed rest, and even though Sam was told the exact same thing, he found himself holding his son in his nursery. 

“So get this, I’m your daddy.” He said to the sleeping bundle in his arms. He could already see so many of Sarah’s features in the baby boy, and it made his heart feel warm with love. “I have no idea how I’m going to do this but I do know I love you so much already. Fair warning: I’m probably going to mess up all the time, and you might hate me when I’m being stupid or crazy or irrational. But I promise I am going to try and be the best daddy to you ever.” 

Hunter let out a sleepy sigh and Sam couldn’t help but melt. “You want to know something baby boy? You have the two best Grandpas in the world. They taught me everything I know. So if I can just be half as good as them, you might just turn out alright.”

“You’re going to be far better at this than I ever was.” Sam turned and looked over his shoulder to see Dean standing in the doorway, looking at Sam with such pride. 

“That’s not true.” Sam disagreed. 

Dean took that as an invitation to come in, and sat down on the ottoman that was in front of the chair Sam was sitting on. “I didn’t know what I was doing the majority of the time, kiddo.” 

Sam looked at his dad incredulously, because if there was one thing he knew for sure was that Dean was a natural at being a parent. “You seemed to have figured it out, because I think I turned out alright.” 

“Yeah, that was dumb luck and a lot of Bobby, Ellen, and Cas.” 

His dad was crazy if he thought that he wasn’t the major reason why Sam and his sisters turned out so well. “Dad is right you know. You sell yourself short a lot.” 

Dean looked away bashfully, he never was one to take to compliments, but Sam didn’t want to let this one rest. 

“Really,” Sam continued, “Emma and Alex have turned out to be the best people I know. And I’ve come all this way and that’s because of you. I know I don’t say this enough or really just appreciate you enough, but you were—you are—the best Dad in the world to me, and you didn’t have to be. Neither you nor Cas had to be.” 

Dean reached out and squeezed Sam’s forearm, trying to stave off his tears. He looked at Sam with serious and loving eyes, “We wanted to be. I just—I just wanted to do the best I could by you.” 

“Thank you. For everything.” Sam’s words were wobbly, and he knew he was going to cry soon. 

“Having the privilege of raising you and watching you become the man you are today has been one of the proudest parts of my life. You’re already an amazing dad and it’s only been one day… Sammy, you’re going to be this little boy’s hero. And I am just so proud of you.” 

Even though Sam had a baby in his arms, he managed to adjust himself enough to pull Dean into a vice-like hug. 

“I love you, Sammy.” 

“I love you more, De.” 

“Not possible.” Dean said as always in response. A few moments later he stood up enough to place a kiss to the top of Sam’s head, much like he use to when Sammy was a boy. “I’ll give you some more time with your kid, but come down soon, dinner is almost ready.” 

Sam sat alone in the nursery for a while, before moving to grab something off the shelf. Slowly he took the old, worn, item back to the chair, and adjusted Hunter so that he could hold it open. 

The book was well loved to the point of nearly falling apart, but Sam could not imagine ever getting rid of it. He looked down at his son, all bundled up in a light blue blanket with small teddy bears printed all over, and thought about how fitting that was. “So my dad and daddy, your Grandpa and Papa, use to read this story to me every night. It’s always been my favorite. I hope that you’ll love it as much as I do.” 

And for the first time, Sam read the story of a small family of bears and a naughty little girl to his son… in the same way his dad’s use to read to him. He couldn’t help but feel like his entire life had been waiting for this moment, for the moment he could share the same memories he’d loved so much as a child with his own child. 

When the book ended, he snuggled his son close to his heart, and kissed his baby soft hair. “You are so loved, baby bear, more than you’ll ever know.”

**Notes for the Chapter:**

> Please, please, please tell me what you thought. I hope this ending was satisfying to you all. 
> 
> I do have some other story ideas in the works/in mind if you'd be interested. 
> 
> Thank you again! 
> 
> <3 Paige

**Author's Note:**

> [Don’t You Wanna Stay](https://archiveofourown.org/works/10634991) Cas has been in love with Dean since high school and when Dean and him go from best friends to falling into a ‘friends with benefits’ relationship Cas thinks he’s happy with the situation. But five years later Cas starts questioning if this is really the kind of life he wants. He loves Dean but he’s sick of getting hurt.
> 
> [Sleep Without You](https://archiveofourown.org/works/10775289/chapters/23899212) Dean and Cas have known each other basically all their life and are very close. Close as in, they sleep (and cuddle) in the same bed together every night but… they deny that they are together. During a weeklong trip with their friends the two start to figure out that there might be something more between them.
> 
> [He Wouldn’t Be Gone](https://archiveofourown.org/works/11261616%20) A year after Cas walked out on their relationship, Dean has to face his ex again at a wedding of all places. Did Dean mention Cas left him the night before he was going to propose? It was going to take a whole lot of whiskey but he was bound and determined to get through the night.
> 
> [There Goes My Life](https://archiveofourown.org/works/12011787/chapters/27182904%20) (WIP) Dean never expected the night he was going to ask Cas to be his that Cas would come home with a baby. 
> 
> [Alright](https://archiveofourown.org/works/11589315/chapters/26046594%20) (WIP) Dean’s grown up with a good head on his shoulders. Cas has grown up being overlooked, never knowing what friendship is. Dean makes it his mission to be the friend he knows Cas deserves.


End file.
